I retired 10 years in and my wife 14 years into the journey. 85 % of my portfolio is 200 year old converted city row homes that are maintenance monsters and we still have enough cash flow to retire from our W-2.

Then connect with some hard money lenders (you can find some here on BP as well as some who are typing this right now) and connect with them to understand their product type, what they like to lend on and requirements.Hard money broker is all numbers game of making relationships and helping those that are looking for financing, it starts out slow but if you get with a few good borrowers and lenders it can be pretty decent money to be made.As an example we paid six figures last year to HM brokers. 

These cases are trickery at best.

Are there any downsides to it?

@Tyler Condon I manage a few properties in the greater Phoenix, AZ area that are adult 55 plus and have great success with them.

@Hank Bank where are you located?

For anyone that is looking at developing or purchasing an STR in Packwood, WA I would take a peek at the numbers that are on the rental sites and the amount of bookings. 

So that’s good.

I recommend you take some courses on underwriting that are geared towards passive investors.

Welcome and happy to share some strategies in Greater Boston area that might work for you and your partner.