It seems like now the differentiator is offering a place larger, and nicer than a hotel - motel room.  

As soon a the "we found mold" card gets played, you immediately offer them to vacate with no penalty to insure their safety. 

For the How I will discuss what to look for regarding local government regulations that allow STRs to thrive, the Where coincides with the How, but I will focus more on what the property and area need in order to make a good STR, specifically in and around the Shenandoah Valley, and the Why will be all about the numbers!

If you're making cash offers command a better price and buy properties correctly.

As an investor and agent in the Florida gulf coast, I just like the feel of Destin and what it offers more than Gulf Shores for the STR market. 

Lot of great replies on here already - only thing that I would add to consider is getting a few outside opinions from realtors, other hosts, property managers, etc. about the medium to long term outlook for STR regulation in your specific area.

You'd need to agree on amount to hold in escrow, and under what very specific terms they are released to which party.

In the meantime consider just storing your cash in a vehicle that offers a stable/consistent ROR.

As the title states I am soon to be leaving active duty with the Marine Corps after 8 years and will be moving back the the great state of Wisconsin, Green Bay to be specific.

I thought you were trying to use it it twice specifically.