Like many military bases the surrounding town is normally small rinky dink with civilians trying to take advantage of military members (loan sharks, auto dealers, gang members, and drug dealers)  Your properties will probably be relatively stagnant due to it only being a military base. 

FYI it's generally going to have to be "dumb person and toddler" proof to close on the purchase ("dump person and toddler" proof is an easy rule of thumb for when an appraiser is required to call something out as a "health and safety" hazard), assuming you are getting a normal mortgage.

Why not just sell it normally right after purchasing it? 

If you refi out of FHA, it allows you to use the low down payment option again for another purchase.If there is a college student market there, you can generally make more than normal leases by renting rooms individually.

Normal to sign off on this contingency once you have seen the conditions and are confident you can get them all.

I don't know on that one but if it is normal 3 tab or typical composite shingles, I always put a layer on top unless it exceeds local code.

Postage is about half the normal rate. 

We've always been shy of real estate investments beyond normal home-ownership because we don't know how to make them work, and we've seen more examples than not of people failing (sadly).

Elise, I am from NJ and my properties are in PA, my PM has never charged that. 1099-MISC is for sub contractor when you pay them, as a PM you are not paying owners because we own the property, we pay you and if anything we should be sending that to the PM, but you should be professional enough to report your income, that income for you is subject to SE tax which you would have to pay. if you are going to charge your customers to cover that cost on top of your normal rate you charge, you may not get any business.

They tend to have affairs and gamble.