so you promise to pay him in 4 months and then “keep it as a rental” how does he get his promised money? 

what about the site itself made that the best path for you?

We have her paying through RentRedi.

Tenants B and C split the front yard, so they each pay $25.Include it in their rent and call it a day.

The contract shouldn't affect your basis, that will be based on what you pay for the property (unless there's some money changing hands outside of closing, which probably wouldn't be documented in the first place).

Yes to the HELOC route, but only if the new property cash flows to pay back the HELOC and its own loan.

You will most likely pay above market rates for the places if the owner is savvy enough.

But why would you pay yourself for work you did on your property?

I will pay for the test and professional remediation if mold is found.Most tenants use mold as an excuse to break the lease.

Use a 3rd party servicer in case the person still have some debt in the property to pay directly to the mortgage company.5.