I think I have figured out why we do not qualify for the STR loophole and why my accountant keeps saying we would not get any money back if we front-end depreciated the home: I have a property management company in place. 

The mistake you're making in the math is on the first number. 20% chance of tripling your money. 

If people have less money they'll travel less.

Business/money has ruined many relationships:(

There are people in here who could have used a handful of that cash and turned it into a lot of money.

First: Define “good.”Second: Why would any owner want to leave money on the table, especially money sufficient enough to make a market deal a “good” deal for the buyer?

@Liliana Bennett most HOA boards are composed of the actual homeowners.Just like there are many DIY owners here on BP, trying to pinch every penny, there are HOA Boards trying to do the same.Guessing your HOA Board members have specifically taken many possible tasks away from the PMC in an effort to save money.

Out of money and options, he licks his wounds and lets it go for back taxes. 

I'd say the Bigger Pockets forums are one of the best places to explore how to put your money to work in RE. 

In the old days this was known as “flash money”.