Seems odd that his wife didn't move in with him or go on the lease when he moved in. 

The FHA househack strategy is fairly common and pretty straight forward, a lot of people have been using this and/or the conventional househack (myself included) so have been on both sides of the table. 

So, renting out my property seems like a good start.

@Robert Frazier Land entitlements are difficult and seems you've now been exposed to appeals and design professional challenges.

Again, not my main goal but it also doesn't seem wise to be short $600/mo. 3.

My limited experience is that anything except the Bronx seems not a bargain.

For now it seems to have stabilized (owned a year). 

They seem to have good number of properties under 100K built in and around 2000's.

From the list of the books that you'd read, it seems that you are focused towards your goal.

And because the PM is not a non-profit, they mark it up 20% and now you get a bill for $287 to change a light bulb.. seems unfair.