By the most important thing (if that's what you're doing) is to have a really good operator who knows the laws, has experience and is above board so they won't leave you high and dry. 

Any luck on motivating realtors in the area to actually get operating expenses/lease agreements for Jackson County specifically George?

Fannie Mae will allow you to transfer the deed to an LLC if you decide to try to go the conventional route, but the loan would still be in your names and you'll need to pay a title company a second time post-closing to do this  for you. 3) I can't speak for the area so no comment there4) If you're self managing, make sure you find vendors you can trust in the area since you won't be able to easily verify if an HVAC guy, plumber, etc. is trying to rip you off and tell you to buy something you don't actually need. 5) Make sure you have clear alignment of goals and a clear operating agreement that spells out what to do if those goals start to not align in the future since you'll be jointly obligated to these properties. 

Therefore, your financial freedom hinges on new companies continuously moving into the city, creating replacement jobs.Companies have many options when selecting a location to set up operations.

I was conducting an extremely seasonal business and after 8 years of operation the business was insolvent. 

The key is to pick a lane—focus on improving as an investor, finding great deals, and letting a solid property manager handle the operations.

I'll also add that Bonnie's group is a great resource with operators from 0-Bonnie.

With running this "business" there will be operational input costs.

Any additional screenings or criteria should be consistently applied to all applicants to avoid potential discrimination claims.Rental application fraud can be a significant threat to the financial and operational stability of running and operating a property.

As long as you're doing that, there's always a risk, and 50 years from now it will probably be illegal everywhere to operate STRs in residential zoning, just like it's illegal to operate a steel mill there.