Sweet old grandma lady gives me a sob story?

I get the feeling by your responses that this tenant just doesn't want things to change because they are cashing in on a sweet rental situation they have right now. 

Zoom out to the bigger flippers who are doing 7+ at once-->they've usually got their procedures and systems in place and there's less value to be added compared with the "switching costs" the flipper would view a new manager as.Following this reasoning I'd say a "sweet spot" approach would be to find people who are flipping 8-20 homes each year and get to know all of them. 

The sweet spot is still a good area but  not amazing so price is somewhat lower but still has investment grade tenant with good cap rate and loan available.

As a prudent investor, I think I am going to stack cash for then next year and see what happens, unless a sweet deal comes about. 

Sweet, now you're up to 60.5k. 

A seasoned property manager could  dispassionately look at that and say ‘it’s an easy clean up, at least it wasn’t wine or chocolate on the carpet.’

However, maybe you have a good wholesaler or agent that can find sweet off market deals nobody knows about.

And leave a bottle of wine for each guest.

Offer them $500, and you will send them a bunch of pictures of the property to save them the drive, something like that is probably the sweet spot.