In my market they just approved a large development for a secondary airport (Brown Field).  

I’m active duty Air Force as well with four properties.

The classic blue cities, SF, LA, Seattle, NYC, Boston are all the best deep water ports in America. 

I am a realtor in Kissimmee Florida area trying to help a friend of mine get into rental arbitrage for Air BNB.

I could also Airbnb it as an eco house as I will make sure air quality is optimal and buy organic mattresses but I'm not sure if Hagerstown would be a potential vacation destination.

Investment Info:
Single-family residence buy & hold investment.

Purchase price: $575,000

5 bed 3 bath house needed a rehab. Purchased, rehabbed, designed, and furnished totally remote! https://abnb....

Any suggestions - especially in regards to high value bills such as electricity during summer when air conditioning is on-  are highly appreciated. 

I'm just going to suggest a few other areas of the city because you got a lot of great recommendations.You might want to consider East Boston because prices are still "affordable" in relation to other parts of the city, the main draw being the airport.

From air rights to zoning laws, it can get complicated but I believe with the right team of people, it’s possible to create opportunities where others didn’t see or gave up soon.  

Offering port-a-potties, well or cistern for water, and some amount of electrical power and wifi located strategically will be enough at first.