My policy is to communicate with owners any time there will be an interruption in their income stream.

Forces like city ordinances/Caltrans/public opinion/eminent domain by states seem to cut the long years of income stream.

If she is renting the house, then it could be an income stream.

I rented out my spare vehicle for 2+ years on Turo, glad to see you're trying to maximize your income streams as well!

it's sounds like your trying to create some type of system to stream line cost estimating in a one box fits all way.

Added benefit, it would be a nice income stream for my retirement. 

I wish you well and hope that you can find additional streams of income that will afford you the opportunity to pay the loans off and live the life you deserve.

What Im not clear on... how many units you have (its psychological loosing that income stream) and its is your first, correct?

I'm a fan of having multiple income streams so I would do both wholesaling and buy-and-hold at the very least. 

For example: Say she trust you with her property, and she expect an income stream for years, to pass to her children - great, here is where i'd negotiate low payments for the first year or two, because I plan a major capital improvements and they would be easier with a little help.