Most “cheaper” and “regular” rental places though don’t generate enough income to worry about taxes anyway so it’s a non issue for most people.

The owner gets cash, the investor signs a sales contract with the owner, and then proceeds to redeem the property and takes possession through a regular sales transaction.  

Due to the market appreciation during the last few years of regular payments I was able to remove the PMI from all loans except for one.

Regular check-ins and setting clear expectations have helped me. 

I feel like those kind of fixes can be estimated when getting a house inspected and appraised. knowing when a new water heater was put in or when a roof was replaced, these all have life expectancies and yes accidents happen but if this is happening on a regular basis for you, like I said, I have concerns.

Batteries last 6-8 months with regular use4.

I know the city inside out and lived there for 20 years, visiting regularly.

And I’d imagine a bit less in closing cost since unlike a regular loan there aren’t normally closing cost but a 0.5% Va funding fee.

A "regular, average" buyer would need to put 20% down on an investment property. 

I agree with all your reasons to offer SF as a seller, just research what methods of conveyance your state has available which offers more seller protections.If I just had a regular note and DofT I don't know if I'd do it.