Your best/safest bet would be a regular lease combined with an option to purchase.

I’m thinks just pay him his regular price for the job and throw him 5-10% finders/gc fee instead of making a 70/30 split or something like that.

I have to go back in and clean things up because the property management company numbers are different from what's in my account.

., guest communication, cleaning, or repairs), and hours worked.

And your cleaners will need to clean out the fireplace ashes each time, make sure the damper is closed, bring wood in or have a pile near the door, whatever.  

I can also allow a tenant to grow with me - just moved a family from a two bedroom to a three bedroom apartment.Personally the only reasons I would choose to invest in multiple markets is a) because I wanted an excuse to go somewhere regularly or b) for economic/geographic diversity.I had the advantage that my home market was good.

My wife and I spend a lot of time together, we take vacations regularly, and I prioritize my health by working out 3–4 days a week and getting 7–8 hours of sleep most nights.

If you are organized enough to forsee hang ups and talk with your GC about potential challenges on a regular basis, two brains are better than one.

I have been part of a regular meetup for a couple years now and it definitely helps ground you in your local market.

Soon after I built the car wash, I was evicted from my leased space where I waxed and cleaned cars.