Stop hanging out with your deadbeat buddies who spend all day drinking, talking sports, and otherwise wasting away.

I have 12-doors in Detroit and I publicly share their historical performance.

I’ve tried VRBO and Furnished Finder, but they didn’t perform well in my market.

I think an equally probable scenario is that we'll convert it to a rental, and then look into a 1031 exchange if we think we can trade into a better-performing asset. 

Sometimes the market changes or can't absorb the rents that they want, so they issue concessions to make it appear as if it's performing as intended.

The bottom line is that past performance is no indication of future returns.

You could just invest in a fund that should out performed what you are doing. 

Stop hanging out with your deadbeat buddies who spend all day drinking, talking sports, and otherwise wasting away.

Handle Legalities:Make sure you have all the permits required for the task you intend to perform.

I think what you’re referring to is a checkbook IRA so you can bypass the custodian when performing transactions/investing and all assets/accounts will be held in the name of a special purpose LLC or Trust which is the instrument that gives you checkbook control.