Since you're in Florida and the laws are much more fair, I'd be willing to take a chance if his background/credit check came in clean. 

Get the remodel done, pay people fairly, and get out of HM as quickly as possible. 

A second shockwave to housing cannot be supported unless we dip below 3.7% unemployment and the median income: house price gets back closer to 6.33 or sub.I think the rates actually show how it'll play out-- a near term dip, a long term buy.

They make things way too difficult compared to a simpler, DSCR solution.The type of lender also plays a large role here. 

It’s priced what would seem like very fair relative to comps in that same neighborhood.

Since it’s been a little while, I’m curious how things played out for you.Just wanted to mention, for a cash-out refinance using a DSCR loan, the max leverage is typically around 75% LTV.

You're developing plays at the collegiate level, but you haven't even played a pickup game with your buddies to see if you like the game or are any good at it.

4) Due to all of the above, high chance they start playing games with other tenants, leading to bigger problems.5) What happens if you have to part ways?

My first duplex Brrr gave me and my wife over $300k equity fairly fast while also allowing us to live at very low cost in an extremely desirable area. 

Remote ownership will be my primary play as I want to keep living in SoCal.