No one is commuting by helicopter….

People live all over, usually a mix of: Connecticut, NJ, Long Island, or Manhattan/Brooklyn. Senior people tend to be further out of the city, although not always, some have a place in the city and out. Some just like nyc and can afford a nice place, it’s really all over 

Those that live out of the city either take advantage of work from home (although you usually can’t all 5 days a week, depends on the firm), car (extremely annoying with or without driver) or train (pretty convenient). 

 

I'm in Charlotte and something I've thought about doing later in my career (when I'm making enough to afford the starting costs) is move out to the mountains about 2-2.5 hours away, then get a nice studio or 1br condo in Uptown. Say I'm in the office 3 days a week, I could get up early Tuesday morning and drive down, stay at the condo Tues/Weds nights, then drive home after work Thursday. Find a good short term rental manager and put the condo on AirBNB/VRBO the other 5 nights out of the week. This is just a theoretical idea I have and haven't crunched the numbers to know if the STR revenue would offset the cost of the condo (or at least get close enough to make it workable).

Something like this might actually work even better in NYC, I know there are restrictions on short term rentals there but also obviously ways around that. 

 
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Yes I’ve done this (minus the rental part, just having multiple places) in nyc. As you note, if you want to rent it out, getting someone to help with this is important. Also, if you need to rental income to make this work it can be risky (as you note nyc has some rules on short term rentals, etc) and you could end up in a tough spot (place doesn’t rent for a while, condo no longer allows you to do it, etc). Condo and co-op boards usually have rules against this. 

What makes this harder as you become more senior is whether or not you plan on having a family. Being away from my kids 2-3 nights a week is a deal breaker for me, so now I just have vacation/weekend places but I don’t regularly commute this way. 

 

The Hamptons guys you hear about live full time in NYC and have weekend homes out east. They'll likely stack WFH days with weekends to get ~4-5 consecutive days out there whenever possible. No one commutes daily from Hamptons - parts of LI just past Queens are doable, although that's hardly a luxury area or a short commute.

 

People with Hamptons homes can wfh whenever they want boyo.  When you are that rich wfh company rules don't apply to you.

 

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