To sum this up - it seems like you guys are jumping in the deep end... and I'd likely suggest to start out small and grow.

I did some deep research on this same idea last year.

I think you should both take a deep breath, read Rich Dad, Poor Dad, and think this one though very carefully.

If it’s too much work, you dislike it, or something doesn’t go right then you are not in too deep, financially.

They will all (or should because it's true) tell you that you can make deep 6 figures in your first year. 

We buy at a deep discount and usually acquire with a loan product that allows us to roll in construction costs. 

I would not recommended moving off-base without BAH (AKA ghosting), as I have seen several Airmen get into a deep hole financially doing that.

List as a sub prime vendor/contractor unless you have deep pockets.

However, it is a very deep lot in an area where houses are being torn down to make way for custom home construction for $1.5-2.5 million dollar homes.

Messy does not equal damaged, as a clean freak I had to learn that after our first couple renters and just breathe deep and let it go.Our "Thing" is little amenities (Snacks and bottled water and a personal note on the counter for them when they arrive) and Absolutely Spotlessly Clean on arrival.