Hypo: You're single, and rich; what U.S. cities would you live in?

Just a fun hypothetical to consider. Let's say you're rich and single; money is not an object. Which U.S. cities would you want to live in? Multiple answers are allowed here, as rich people tend to have multiple homes.

I'm gonna break it down by seasons.

Spring and Fall: NYC
Summer: Chicago
Winter: L.A.

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Comments (127)

Funniest
Sep 29, 2017 - 1:05pm

Somewhere far away from

a) illegal immigrants
b) black people enamored with hip hop culture
c) blue collar workers
d)anybody who drives a pick-up truck
e)people without a college degree or any sort of history of achievement
f) white trash
g) people who've never been outside the USA
i)deeply religious people
j) anyone with a tattoo visible when casual clothes

Manhattan penthouse, Aspen, Beverly Hills, Stanford/Atherton/Los Gates California. A mansion in the Hamptons wouldn't hurt.

Oh by the way I grew up in Cupertino California. Apple's HQ was down the road from me. I was blessed to be surrounded by some extremely world class personalities during school. My family circle consisted of millionaire venture capitalists, chairman of the board types, engineers and doctors. My classmates were sons of gastroentrologists, anesthesologists, politicians close to heads of states. In high school one of my classmates got married to a guy has an $8 million private jet and whose grandfather was on the Forbes List. My dad's best friend's daughter is a neurosurgeon and so is her husband. So pardon me if I come across as snobby but that's just the environment I grew up in.

If I'm hated for the views, not my problem. Once you grow up in Silicon Valley most of a-j seem like prehistoric cave animals. I'm not racist. I've been to Hong Kong, Singapore, the Middle East, Europe, Mexico, Korea. I've even seen the American South - New Orleans and Mississippi to be precise. I've come to the conclusion after seeing the world there is a reason stereotypes exist and why preconceived notions are fine.

All I'm saying is I'm trying to stay away from people like :
https://www.liveleak.com/view?i=22e_1504396576

D.I.
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Best Response
Sep 28, 2017 - 3:24pm
oligarch:

a) illegal immigrants
b) black people enamored with hip hop culture
c) blue collar workers
d)anybody who drives a pick-up truck
e)people without a college degree or any sort of history of achievement
f) white trash
g) people who've never been outside the USA
i)deeply religious people
j) anyone with a tattoo visible when casual clothes

I hope you find this place and go there, because it will keep you far away from me.

"Son, life is hard. But it's harder if you're stupid." - my dad
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Controversial
Sep 28, 2017 - 11:52pm
oligarch:

Somewhere far away from

a) illegal immigrants
b) black people enamored with hip hop culture
c) blue collar workers
d)anybody who drives a pick-up truck
e)people without a college degree or any sort of history of achievement
f) white trash
g) people who've never been outside the USA
i)deeply religious people
j) anyone with a tattoo visible when casual clothes

Manhattan penthouse, Aspen, Beverly Hills, Stanford/Atherton/Los Gates California. A mansion in the Hamptons wouldn't hurt.

Monkey shit for polluting my thread with your racism, bigotry, and ignorance.

Sep 29, 2017 - 7:42am

monkey shit for accusing me of racism.

How am I racist ?

I dislike white trash and black people enamored with hip hop culture. I didn't say I dislike white people or black people.

Suck it up.

D.I.
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Sep 29, 2017 - 8:01am
oligarch:

Somewhere far away from

a) illegal immigrants
b) black people enamored with hip hop culture
c) blue collar workers
d)anybody who drives a pick-up truck
e)people without a college degree or any sort of history of achievement
f) white trash
g) people who've never been outside the USA
i)deeply religious people
j) anyone with a tattoo visible when casual clothes

Manhattan penthouse, Aspen, Beverly Hills, Stanford/Atherton/Los Gates California. A mansion in the Hamptons wouldn't hurt.

Please go buy an island to then move to permanently. For some reason I believe you actually feel this way and not leveling here.

Get your facts first, then you can distort them as you please.
Sep 29, 2017 - 8:06am

are you guys for real ?

Looks like most white people in America don't even know what their own country is like.

Everybody in Aspen, Beverly Hills, Manhattan, Malibu, Silicon Valley's posh areas DOES NOT live next to:
a) illegal immigrants
b) black people enamored with hip hop culture
c) blue collar workers
d)anybody who drives a pick-up truck
e)people without a college degree or any sort of history of achievement
f) white trash
g) people who've never been outside the USA
i)deeply religious people
j) anyone with a tattoo visible when casual clothes

I don't need to buy a freaking island. Oh and by the way. I'm pretty sure all those WASP elite in the Hamptons concur with me.

Why does Bill Gates travel the whole world when he can spend his time at some trailer park in California with his white cousins ? Probably because he thinks just like me.

D.I.
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Sep 29, 2017 - 1:24pm
oligarch:

Oh by the way I grew up in Cupertino California. Apple's HQ was down the road from me. I was blessed to be surrounded by some extremely world class personalities during school. My family circle consisted of millionaire venture capitalists, chairman of the board types, engineers and doctors. My classmates were sons of gastroentrologists, anesthesologists, politicians close to heads of states. In high school one of my classmates got married to a guy has an $8 million private jet and whose grandfather was on the Forbes List. My dad's best friend's daughter is a neurosurgeon and so is her husband.

Apologies for the thread hijack, but I can't not comment... Neat story about your classmate's grandfather and your dad's friend's daughter, but what have YOU done in life? Your profile suggests you work in non-profit, and your post history indicates you're intimidated by women in finance and have only one friend.

You're free to have whatever views you want, and we can agree or disagree with them, but you're coming across as though you're so superior than most others when I can't really gather what you've managed to accomplish in life to justify such a lofty self-valuation.

Sep 29, 2017 - 9:54pm
oligarch:

Somewhere far away from

a) illegal immigrants
b) black people enamored with hip hop culture
c) blue collar workers
d)anybody who drives a pick-up truck
e)people without a college degree or any sort of history of achievement
f) white trash
g) people who've never been outside the USA
i)deeply religious people
j) anyone with a tattoo visible when casual clothes

Manhattan penthouse, Aspen, Beverly Hills, Stanford/Atherton/Los Gates California. A mansion in the Hamptons wouldn't hurt.

Oh by the way I grew up in Cupertino California. Apple's HQ was down the road from me. I was blessed to be surrounded by some extremely world class personalities during school. My family circle consisted of millionaire venture capitalists, chairman of the board types, engineers and doctors. My classmates were sons of gastroentrologists, anesthesologists, politicians close to heads of states. In high school one of my classmates got married to a guy has an $8 million private jet and whose grandfather was on the Forbes List. My dad's best friend's daughter is a neurosurgeon and so is her husband. So pardon me if I come across as snobby but that's just the environment I grew up in.

If I'm hated for the views, not my problem. Once you grow up in Silicon Valley most of a-j seem like prehistoric cave animals. I'm not racist. I've been to Hong Kong, Singapore, the Middle East, Europe, Mexico, Korea. I've even seen the American South - New Orleans and Mississippi to be precise. I've come to the conclusion after seeing the world there is a reason stereotypes exist and why preconceived notions are fine.

All I'm saying is I'm trying to stay away from people like :
https://www.liveleak.com/view?i=22e_1504396576

ROFL!

Gr8b8m8.

Literally one of best shitposts I have seen on this website.

Also, Username checks out.

Sep 30, 2017 - 12:11am

how can you grow up in silicon valley and subscribe to those views? the whole ethos is that weird and crazy people from any background can come together, free of judgement, and build great products. you clearly don't understand what silicon valley is about and what makes it magical.

Oct 3, 2017 - 9:45pm

You need a job where you don't open your mouth very often.

I wish I could meet you in real life and put you in a lab/zoo, you would be a very interesting specimen to examine. My guess is you're not a full psycho/sociopath, because those guys are typically too smart to play 50k of their parents money on a single trade while in HS/College (see his other posts).

You idealize the wealthy yet have contributed nothing to society, and look down upon people who you know nothing about based on broad stereotypes. You quite honestly sound like the worst type of person.

Oct 4, 2017 - 9:36am

I am NOT the worst type of person. I'd never call my daughter a piece of ass via national media nor would I mention grab her by the pu$$y like DT has.

All I said is I want to stay away from unsophisticated poor people.

D.I.
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Oct 4, 2017 - 8:24am

Someone's trying to hit the monkey poo record.

Good luck, and enjoy living with your fellow candyasses.

Oct 5, 2017 - 5:03pm
The Real Donnie Azoff:

I'm going to jump in because I have to ask...

a grown man married this chick while she was in high school?

She married a third generation heir. He didn't earn it or buy it with his own money. Obviously no way a 24 year old can afford a $8 million plane. His family's empire spans more than three countries has a jet for their senior level management who travel all over the world.

The plane belongs to the corporation - which belongs to the family - but since the tail has the family name on it - it's just as well his.

Gorgeous bird though. Dassault Falcon 2000.

D.I.
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Oct 5, 2017 - 8:00pm
oligarch:

Somewhere far away from

a) illegal immigrants
b) black people enamored with hip hop culture
c) blue collar workers
d)anybody who drives a pick-up truck
e)people without a college degree or any sort of history of achievement
f) white trash
g) people who've never been outside the USA
i)deeply religious people
j) anyone with a tattoo visible when casual clothes

Manhattan penthouse, Aspen, Beverly Hills, Stanford/Atherton/Los Gates California. A mansion in the Hamptons wouldn't hurt.

Oh by the way I grew up in Cupertino California. Apple's HQ was down the road from me. I was blessed to be surrounded by some extremely world class personalities during school. My family circle consisted of millionaire venture capitalists, chairman of the board types, engineers and doctors. My classmates were sons of gastroentrologists, anesthesologists, politicians close to heads of states. In high school one of my classmates got married to a guy has an $8 million private jet and whose grandfather was on the Forbes List. My dad's best friend's daughter is a neurosurgeon and so is her husband. So pardon me if I come across as snobby but that's just the environment I grew up in.

If I'm hated for the views, not my problem. Once you grow up in Silicon Valley most of a-j seem like prehistoric cave animals. I'm not racist. I've been to Hong Kong, Singapore, the Middle East, Europe, Mexico, Korea. I've even seen the American South - New Orleans and Mississippi to be precise. I've come to the conclusion after seeing the world there is a reason stereotypes exist and why preconceived notions are fine.

All I'm saying is I'm trying to stay away from people like :
https://www.liveleak.com/view?i=22e_1504396576


Where's"h"?
Sep 28, 2017 - 3:59pm
Abhizzy:

Chicago doesnt believe in Fall/Spring.... We tend to go from WINTER to SUMMER to WINTER.... Our fall season has been overwhelmed by our repressed summer finally showing up the past few days.

Chicago is a 2-season city. It starts getting cold in October and stays that way until early June. Heck, I've experienced so many days in even June where the temperature in Chicago doesn't go above 70.

The winters are brutal, but the summers are perfection, the embodiment of what a city should be.

Sep 28, 2017 - 3:56pm
jankynoname:

I'd probably spend most of the year in La Jolla, with chunks of summer/fall in Boulder or somewhere else along the front range. Would probably also need a small place on Oahu north shore as well for variety.

I love San Diego; probably the best weather in the country. But it's pretty boring for single men. Awesome place if you're rich and married.

Sep 29, 2017 - 7:57am

This.

“Bestow pardon for many things; seek pardon for none.”
Sep 28, 2017 - 4:03pm

I have a weird list, because all other things equal, I'd rather be outside of a city than in it. I wish I had about 800 square feet, with wi-fi and a backpack, in:

  1. Roche Harbor, WA
  2. Sunriver, OR
  3. Whitefish, MT
  4. Moab, UT
  5. Truckee, CA
  6. Carmel, CA
  7. St Simon's Island, GA
  8. Pinehurst, NC
  9. Bar Harbor, ME
"Son, life is hard. But it's harder if you're stupid." - my dad
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Sep 28, 2017 - 4:09pm

Maine and the rest of New England is beautiful. A shame the tax rates are pretty high from what I understand, except for New Hampshire, I'd otherwise love to retire there.

Quant (ˈkwänt) n: An expert, someone who knows more and more about less and less until they know everything about nothing.

Sep 29, 2017 - 9:17am

You are right about the taxes in NE. Maine has marginal income tax brackets of 0%, 5.8%, and 7.15% of your net income after federal taxes. The state also has an average sales tax of 6%.

New Hampshire has no income or sales tax, but the property tax are relatively high.

Overall the COL is pretty low compared to the rest of the US and the quality of life is incredibly high.

Array
Sep 28, 2017 - 4:10pm

Spring and Fall: Seattle
Summer: Seattle
Winter: Seattle

Quant (ˈkwänt) n: An expert, someone who knows more and more about less and less until they know everything about nothing.

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Oct 6, 2017 - 12:46pm

I've never been tbh, I just know OP isn't a fan. Doesn't sound all that bad, but that's just anecdotes so it might suck.

Quant (ˈkwänt) n: An expert, someone who knows more and more about less and less until they know everything about nothing.

Sep 28, 2017 - 4:29pm

My list is boring and pedestrian, but I can't kid myself: I'm boring and pedestrian.

Summer/Fall (June 1st - October 31st)

I would cycle between:

-Portland, Maine

-Portsmouth, NH

-Burlington, VT

I'm not a city person, and all three of these are close to tons of great recreation and have all the amenities I would want/need (decent food/beer scene). I'm a simple dude. Plus it's hard to beat northern New England in the summer and fall.

Winter: (Nov. 1st - March 31st)

-Vero Beach, FL

or

-Somewhere on the Gulf Coast, FL

Great weather, solid location. As a longtime resident of the cripplingly cold north, this would be ideal from November - March.

Spring (April 1st - May 31st)

-Charleston, SC

I wanted to work Charleston in here somewhere, and I think this would be the ideal time (before it's super hot).

Oct 9, 2017 - 10:29pm

Not sure about your winter choices, but summer and spring are extremely on point.

Quant (ˈkwänt) n: An expert, someone who knows more and more about less and less until they know everything about nothing.

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Sep 28, 2017 - 4:46pm

Somewhere in the hill of Silicon Valley California. the avg IQ there, the number of smart people, and the diverse pool just reeks of globalist elite .

While San Francisco is indeed a shithole - the hills of Pleasanton, Los Gatos are unparalleled in beauty.

Sep 28, 2017 - 6:03pm
jankynoname:

in what universe is SF a shithole? I mean I agree with you that there are some very nice 'burbs out here, even the urban area is still pretty sick.

SF is beautiful in terms of the natural scenery, but the city is a mess due to incompetent governance and terrible policies. You have bums literally shitting and pissing on the streets, rent is out of control, and along with Seattle is the worst major U.S. city for single straight men. Even if I were a billionaire, I would not have a home in SF.

Sep 30, 2017 - 8:03am

I currently live in SF and there are parts of the city that have been turned into literal shit holes due to the police having their hands tied by a DA that won't prosecute property crime and drug use/low level sale. It's sad but true but other than that SF is great to live in.

To reply to the OP:

Ski in/out condo in Jackson Hole

House on 17 Mile Drive overlooking the ocean/pebble, cypress point membership included

House in Greenwich/Westport with access to a helipad at the house and in Manhattan

Apartment in Central Park West

House on Martha's Vineyard (another helipad)

Oct 3, 2017 - 10:18pm
papertiger:

Somewhere in the hill of Silicon Valley California. the avg IQ there, the number of smart people, and the diverse pool just reeks of globalist elite .

While San Francisco is indeed a shithole - the hills of Pleasanton, Los Gatos are unparalleled in beauty.

My friend lives in The Cats

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee

Sep 28, 2017 - 5:03pm
  • Houston, Texas
  • Austin, Texas
  • Dallas, Texas
  • San Antonio, Texas

jk.... I would probably just explore the country, east coast & midwest being the main areas as I have not spent much time in those regions. If I had to live somewhere though it would be in TX, that's where my family is. If I'm rich I can just vacate anywhere.

Array
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Sep 28, 2017 - 6:23pm

If you're trying to live the playboy lifestyle I'd say that NY and LA/MIA are your only good options.

Personally, if I didn't have to work I'd live in LA most of the time. Lot going on, I like driving and I like cars so the distance/traffic isn't a big problem for me, the girls are straight fire, the weather is great, and it has some of the best food in the world. I also like fitness culture and think it would be pretty cool to be in a place where a lot of exciting stuff is going on. Again - Girls - LA........

Sep 28, 2017 - 7:20pm
TrackBack:

If you're trying to live the playboy lifestyle I'd say that NY and LA/MIA are your only good options.

Personally, if I didn't have to work I'd live in LA most of the time. Lot going on, I like driving and I like cars so the distance/traffic isn't a big problem for me, the girls are straight fire, the weather is great, and it has some of the best food in the world. I also like fitness culture and think it would be pretty cool to be in a place where a lot of exciting stuff is going on. Again - Girls - LA........

I have visited LA a lot but have never lived there. I hate driving, but the city is super intriguing for the reasons listed above. Amazing weather, great Mexican and Asian food, not too expensive, and exactly my type of women.

What are the best areas for single men making good money? I would think Santa Monica, Beverly Hills, and West Hollywood?

Sep 29, 2017 - 4:47pm

If you are single, on the younger side, and looking to live it up a little bit, I'd say your two best spots are Venice / Santa Monica (the part of Santa Monica that is adjacent to Venice) or the Beverly Hills / West Hollywood adjacent area. Rent a bungalow in Venice or a house in WeHo adjacent with a couple other similar guys and you'll be set up nicely.

The WeHo area has more of a classic "Hollywood" feel -- lots of people trying to make it in entertainment, lots of people trying to be "seen," lots of sceney clubs, the Sunset strip, etc. Venice has more of a bohemian, beachy vibe with trendy bars instead of clubs. Both scenes will have plenty of beyond gorgeous women walking around.

Driving isn't as big of an issue as people think. You'll likely stick around your neighborhood most of the time.

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Oct 3, 2017 - 10:22pm
Rufus1234:

TrackBack:

If you're trying to live the playboy lifestyle I'd say that NY and LA/MIA are your only good options.

Personally, if I didn't have to work I'd live in LA most of the time. Lot going on, I like driving and I like cars so the distance/traffic isn't a big problem for me, the girls are straight fire, the weather is great, and it has some of the best food in the world. I also like fitness culture and think it would be pretty cool to be in a place where a lot of exciting stuff is going on. Again - Girls - LA........


I have visited LA a lot but have never lived there. I hate driving, but the city is super intriguing for the reasons listed above. Amazing weather, great Mexican and Asian food, not too expensive, and exactly my type of women.

Not too expensive? Hmm... real estate is probably cheaper than NYC and SF, but its no San Diego in terms of low COL.

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee

Sep 28, 2017 - 8:32pm

In the bedroom of a custom Airbus A380 over the ocean somewhere with a bunch of supermodels on board.

Follow the shit your fellow monkeys say @shitWSOsays

Life is hard, it's even harder when you're stupid - John Wayne

Sep 29, 2017 - 3:01am
Rufus1234:

Just a fun hypothetical to consider. Let's say you're rich and single; money is not an object. Which U.S. cities would you want to live in? Multiple answers are allowed here, as rich people tend to have multiple homes.

I'm gonna break it down by seasons.

Spring and Fall: NYC
Summer: Chicago
Winter: L.A.

Denver is pretty money year round.

Sep 29, 2017 - 6:21am

Because n00bs

GoldenCinderblock: "I keep spending all my money on exotic fish so my armor sucks. Is it possible to romance multiple females? I got with the blue chick so far but I am also interested in the electronic chick and the face mask chick."
Sep 29, 2017 - 6:23am

I'll thank Matrick for letting me know of Berggruen and his lifestyle. That's the lifestyle I want to take - the homeless billionaire, staying in hotels and (unlike him), scratching my bum and crotch in hotel lobbies. Also, making dimes think I'm broke af.

GoldenCinderblock: "I keep spending all my money on exotic fish so my armor sucks. Is it possible to romance multiple females? I got with the blue chick so far but I am also interested in the electronic chick and the face mask chick."
Sep 29, 2017 - 7:00am

The sad thing about Oligarch's answer, reality says that's how most rich think. They stay the fuck away from minorities and the poor in general.

Never discuss with idiots, first they drag you at their level, then they beat you with experience.

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Sep 29, 2017 - 2:03pm

That's how most of the coastal rich think. Those of us in the interior actually understand that there's nothing wrong with "rednecks" and that how people choose to live their lives within their culture is not something that should be shamed.

@oligarch is the reason we'll all be put up against the wall when the revolution comes.

University of Chicago
Oct 4, 2017 - 10:26am

Dude cut yourself some slack.

Can't you tell this is the most hilarious troll of all time?

I am probably the most backwoods mf*cker in this thread and I am now rolling, laughing for the second time reading it.

The liveleak shit puts it over the top.

Sep 29, 2017 - 1:11pm

Assuming I have no family and am looking to get weird:

Summer: Amalfi Coast and/or Greek Islands
Winter: Las Vegas
Spring/Fall: some combo of Buenos Aires/Rio/Vallarta

"Who am I? I'm the guy that does his job. You must be the other guy."
Oct 10, 2017 - 3:25pm

Yeah not gonna lie didn't register that part of the prompt.

"Who am I? I'm the guy that does his job. You must be the other guy."
Oct 3, 2017 - 11:20am

I'm a big fan of Dallas. I'd probably throw Miami into the mix. NY, DC, SF, LA, all out. Just because I'm rich in this scenario doesn't mean I'd want to deal with high taxes, hipsters, and snobs.

Oct 4, 2017 - 1:15pm

Dallas is pretty decent as well. Miami / Soflo culture is a lot about flashing money, having tattoos, etc. Not really big on that culture (but the parties down there are amazing). I think Houston has a better airport than Dallas which would also be pretty important.

Oct 5, 2017 - 7:53pm
TheGrind:

I'm a big fan of Dallas. I'd probably throw Miami into the mix. NY, DC, SF, LA, all out. Just because I'm rich in this scenario doesn't mean I'd want to deal with high taxes, hipsters, and snobs.

Aside from no state or city tax, I don't see the appeal of Dallas for single men. Women down there marry super young, so the dating scene is pretty mediocre, and the overall social scene and nightlife aren't that great. You're also not near any big body of water.

Dallas is horrendous for single men. People get married super young down there, and the city lacks meaningful night life, c

Oct 3, 2017 - 6:08pm

Del Mar / La Jolla / Rancho Santa Fe area of San Diego

Homes for a decent one runs around $1m starting, going up towards 2-5m+ depending on what you are looking for.

I'd personally stay in La Jolla/Del Mar for the beaches, cool weather, and diverse community. There are weekend groups in all three locations where they meet and do pretty cool things.

Oct 5, 2017 - 12:33am
HuntNKill:

Del Mar / La Jolla / Rancho Santa Fe area of San Diego

Homes for a decent one runs around $1m starting, going up towards 2-5m+ depending on what you are looking for.

I'd personally stay in La Jolla/Del Mar for the beaches, cool weather, and diverse community. There are weekend groups in all three locations where they meet and do pretty cool things.

Yeah I lived in Encinitas for a year - cool area

"If you always put limits on everything you do, physical or anything else, it will spread into your work and into your life. There are no limits. There are only plateaus, and you must not stay there, you must go beyond them." - Bruce Lee

Oct 4, 2017 - 10:00am

Chicago

“Elections are a futures market for stolen property”
Oct 4, 2017 - 11:14pm

Summer: Newport Beach and San Diego

Autumn: Chicago

Winter: Lake Tahoe

Spring: Freeport, Maine

"Work ethic, work ethic" - Vince Vaughn

Oct 6, 2017 - 12:30pm

Scottsdale, Arizona. Close proximity to Arizona State University, incredible weather year round (3 months of 100+, so maybe go somewhere else in the summers), bikinis year round, nightlife quality 1 tier below Vegas, very low COL, 3 hours drive to skiing, 6 hour drive to Mexico, 6 hour drive to San Diego

Oct 6, 2017 - 1:14pm

Likely a pad in at least one of either NYC, LA or San Fran. If for no other reason than if you have that kind of money, you're likely working in one of these areas.

Also surprised I haven't seen London mentioned more. Its a great town, full of people from around the world and it puts you in good proximity for easy visits to other points in Europe.

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