Chicago is losing housing stock at an alarming rate. 

from a laptop or mobile phone on one of my SFR's (internet must be hooked up, but most tenants do it anyway and like to be able to monitor the outside of the house remotely, even if there's nothing going on.)

Under Alabama law, that is a VERY dangerous play and you could end by losing money.You also cannot sit back and let him build the house and say "Thanks."

Single-gender homes are only for transitional housing (like soberliving houses, halfway houses, etc). 

If the house was built in the 50's or earlier than you probably have cast iron pipes.

He was also in escrow to sell the house as a busted flip, as-is.

That journey started in 2016 when I bought a duplex to house hack.

@Derick Jennings Without knowing more about your situation, I'd likely recommend a house hack, a strategy I wish I would have known about when I got started.

@Jacob Flaxman, I am not familiar with this market, so take what I have to say as more of a general comment.My first thought is $250k to build a two story, two bed "house" will cost more than $250k. 

The city has already approved the permits, and the cost to rebuild the 1200 sqft. house is estimated at around $120K.