What is crazy though, is I am able to keep 85% occupancy through the year and most guests stay 2-3 months so only 5-7 turnovers a year.

This scales your investing.Forces you to network and depend on a team leading to relationships = more businessForces you to develop communication and business systems to stay on trackConsNot as easy to physically be on site if neededReally it comes down to how you want to invest.

After being in Cleveland Hts, probably one of our biggest mistakes was staying there so long with both of us driving a lot.

I'd be looking to go where I could stay debt free and greatly increase my return on asset and cash flow.

It's going to take a few months for the score to get better and stay better; 50K is significant credit card debt, so work on a budget. 

I like the idea of staying local first. to expand out of state is difficult and you must have a competent and trustworthy team in place which is not easy. 

Nothing to add to the education piece but I'll definitely stay engaged with this conversation.

@Matthew TeuschelThe "risk" with Subject To is that the owner continues to make payments.You're buying Subject To the existing mortgage staying in place.

If you're operating a short term rental that focuses on <30 day stays, you should consider a Schedule C business.The 2018 Schedule E tax forms has a box for Short Term Rentals but I'm not clear what they have in mind.

Zillow says $125 rent increase equals a move and $50 increase is a common increase for tenants who stay.