That is not luck, that is not random, that is suicide.So conclusion,  the people you are trying to skip trace (and pay money for to skip trace) are not just "a bad " audience.They are the worst possible audience.

Knowing I didn't want to rent it out for at least 2 years, I didn't put my name on the renting list which I now know was a bad move.

I currently use a property manager but they are very bad in tenant placements who do not answer calls or inquiries from Zillow.

Hello folks,Wanted to get some of the key criteria folks use in evaluation whether a deal is good or no. I for one built a simple chrome extension to see if the mortgage is less than rent and accordingly provide that ...

The older homes there aren't as bad (2k to 3k). 

This attracts a higher-quality renter, ensures funds are available to maintain the home, and reduces the risk of major losses.

Buy quality, if that means every 2-4 years not annually so be it.

And most people don't understand that S8 rents can change, usually on an annual basis as tenants are reassessed.How bad can it change?

That's not a bad idea - just strike a business contract.

If you flip your flooring upgrades and appliances will probably need to be of higher quality vs a rental.