For the multi-family, lenders typically count about 75% of projected rental income toward your debt-to-income ratio, which should help if the property is cash-flowing.

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

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

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

I used a realtor that specialized in rehab properties.

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

How long do you intend to occupy the property?

$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

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

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.