That's what the "old grey haired" investors that I've spoken with had to contend with doing.  

Great stuff!

We hear about off market stuff fairly frequently.

Lets say you are waiting to get that cash flow flip in 5 years; a new roof, HVAC, routine upgrades and the other stuff I mentioned can leave you in the whole another 5 years once it collectively adds up.

I’d prefer not to switch so I’m trying to figure out hire to track this stuff, any recommendations?

This kinda stuff is normal low income tenant behavior.

I really think the other stuff on your list is extremely negligible. 

You don't sell refrigerators to Eskimos, hair curlers to Nigerians, or rentals in a market with no renters.2. 

I would better spend money on custom service like https://essayyoda.com/custom-service/ than on some doubtful stuff.

Just the stuff I needed to read, so thank you.