Speed Run to $200k/yr Passive Income

As someone who actually owns a few STR properties I thought I might weigh in for what it's worth. If you're able to get good deals and execute a decent strategy you can get pretty good returns (10-20% cash on cash / 20%+ IRR) in an appreciating area while using a property manager to make it a passive investment. It's definitely not fast though and it requires a lot of capital (down payment + furnishings) and has high expenses (management fees, utilities, etc.). I can't speak to a lot of the content on social media, but from my perspective STRs can be a pretty nice way to approach individual RE investing as you generally get more cash flow than traditional long term rentals.

As a data point, I live in a MCOL / growing city and implement pad splitting for my STRs and each one (bought for $150-$300k with traditional financing) produces $10-$15k in annual cash flow. I plan on purchasing a handful more in order to reach $100k in passive income with my goal to do this in 3-5 years - this will probably take a portfolio of 8-10 rentals to cash flow that consistently. I'm sure there are smarter and faster ways to execute this (e.g., no money down, HELOC's, creative financing, more attractive markets, etc.), but I'm ok with sticking to local markets and putting more equity in my deals. Also, for what it's worth I'm not 100% in STRs - my portfolio is about 2/3 index funds / the market and 1/3 RE. 

Let's say $100k saved up to start plus an additional $50k/yr until goal is achieved

Bernie Madoff checking in with the split-strike conversion strategy ;-)

not a bad strategy

trustmeimanengineer

Put the 100k into a dividend ETF or create your own that you manage. AT&T and Verizon both give 6.5% or more in annual dividends. If you're adding 50k a year, just reinvest those for a few years and add a few other blue chip stocks. You'll get to 25k passive income via dividends in like 3-4 years if not faster. Then you can set it and forget it while reinvesting. I'd make it more diversified than just a few stocks, but Exxon and a few others also give good dividends. 

Faster way may to be just buy stocks/ETFs and just gain the appreciation over the next 5 years. Some experts I've seen think we are 1-2 years from the "bottom" so DCAing now will return exponentially in 3-5 years. Probably expect less immediate return but gain more return over the long-run as your capital gains should be lower too.

Quickest way would be to go into real estate. Buy a duplex, live in one half while renting the other half. Depends on the local area, but you should be able to get 1 to 3 with 100k down. Then you're cash-flowing 500/month per property on the low end after mortgages, taxes, and insurance are paid. This is not really passive as there will be some labor and time required to invest. Once interest rates come back down, you'll not only have equity in the duplex or rental properties but also whatever appreciation too.

This is something I am looking to do.  I know how to do basic repairs - electrical, plumbing, drywall, flooring.

I may look into getting a GC license to do side gigs as a HandyMan.