My father did this in Portland on two properties, for elderly people I think. 

would get estimates and see how long to recover the money and your long term plan for the property

It allows you, the wholesaler, to transfer your rights to purchase the property to an investor.

Our initial goal has been to buy a property every time the Army relocates me (roughly every two years) and rent it out afterward.

$10K seems like a nice, round number...Finally, if you have $250K in cash, I would not put it all into a single property / single dealHope this helps... happy to help further

There are plenty of websites that can give you a good idea of property values in your area.

Managing tenants is probably the most frustrating task of all the task associated with owning rental property.  

I’ve had a great experience with Brian Hartsell at key properties for my vegas properties. 

I would take out a private loan on the paid off property to get the other one squared away

Since the yard is already rough, I would keep the shed and see how it works out.Consider adding something to the lease that permits you to remove it from the property if it becomes problematic.