The first red flag about this "deal" is that you're losing money every month and not actually cash flowing. 

The red flags are different.

Sorry to dissect this, but a lot of red flags here, and it just isn't adding up. 

That's some beautiful stabilization in progress!

(3) What kind of questions should I ask in order to reveal any potential red flags on my end?

The beauty of Facebook is the ability to screen the tenants beforehand .

It may be expensive to to get into but you if you can afford it, bel air should be good purchase.Other areas to consider around APG are aberdeen ( home of Cal Ripken jr ) Havre de grace ( beautiful bay town on the water ) Edgewood and joppatown (my old stomping grounds)

I've red here that people won't buy if the house makes less than let's say 250usd/month. 

You either redo all together or use beauty band traditions or diffident treatment on extended portion.

The home also turned out beautifully.