one option is to continue renting out all four properties to cover mortgage payments and generate passive income.

So YOUR investment of $200,000 is now worth $1 million after 15 years, AND you own an income producing property that is completely paid for!  

Section 8 is a government program that allows you to rent properties to lower-income residents in the Section 8 program. 

I had to put myself under Electrical once they notified me of no longer being in business.Because of that, and because it took a year to get a response from them, I have had my house sitting vacant, not generating income, and I want to sell it to buy something closer to my house.

Your primary residence is a liability, not an asset (it does not generate income), compared to an income property which is an asset not a liability.A few things you are missing:1.

I have nothing against me, no criminal record, good credit, job, income, savings, single male, no kids... could the HOA decline my highest offer the property to whoever they choose? 

For my calculations I take 15% of my potential gross income (PGI).

Very frustrating selling multiple homes a year with nothing but taxable events to pay on but maybe that's all it is. 

One of the reasons for this is the ability to generate passive income.

Increase your income, reduce your expenses, save consistently until you build up enough to invest.