I have read I will need to use a third party service to make this happen.  

Reading thru Vail Resorts annual report the other day and looks like they loose money. 

realities of being self employed.. 

The higher credit, higher income, gainfully employed S8 tenants are choosy about where they live and do not want to live in a bad, high crime area.By buying in an area that appeals to high quality S8 tenants, the arbitrage that you might see between S8 being higher than market might disappear.So that being said, it’s more important to lead by location than strategy.Happy to talk further if you like.  

I also have ~$20k that I've resigned for the scripted "mishap" that always comes up after purchase...lolI've read a number of other threads and I've seen a fair amount of talk about Ohio.

If this were my property, I’d run a detailed rental analysis (from what I’ve read in Forbes) to see if the short term route could outpace traditional leasing.

Some local lenders familiar with Gainesville’s market (from what I’ve read in Bloomberg) like SunState Federal Credit Union and Ameris Bank have been mentioned favorably latley and might be a bit more flexible if they understand the repositioning story behind your property.

Not doing anything to get better education or employment opportunities.

As you read these books, watch the BiggerPockets podcasts.

From what I read in The Economist, these Sun Belt regions often see steady population growth which can drive healthy rent appreciation.