This is a very important distinction that a lot of investors miss - treating sellers of this nature, like dollars and cents investors, is a mistake and likely a big turn off to the seller.

Sounds like you are a natural negotiator.They might be most apprehensive about giving you title on all these properties for low to no money down.

However, what I have found with folks who buy STRs as investments are generally pretty active in their investments by nature.   

Now I want to add something to the conversation of a more proactive nature. 

They will keep pests down, are good natural weed control, and friendly neighbors.As long as your tenants are responsible, and it sounds as if they are, encouraging them to keep bees will only improve both of your situations.

Just for arguments sake, it's the very nature of our system that breeds incomitance.

I really enjoy building relationships and speaking with others so naturally I enjoy selling, but again would just love to be in a position where I get to learn about real estate full time!

My worry is that Section 8 may stifle the natural appreciation of rent prices to keep up with the market.

The con with this strategy is that you are converting income that is rental in nature to ordinary income(may be subject to SE taxes).The pro with this strategy is that it potentially opens you up to health insurance / retirement account deductions.

If you live in a competitive market where renters naturally have utilities included, then you "MAY" consider it but unless the cost of the rent is considerable enough to offset the utilities and still cashflow, I would put it on the renters.