Then, pack the white oakum, and re-pour lead or get white oakum and a home depot tube below (NOT RECOMMENDED). http://www.homedepot.com/p/10-3-oz-Plastic-Seal-25...If you have the tools go for it, otherwise, don't bother. 

A lot of buildings in Chicago are quite old, which is not necessarily a bad thing, but be on the lookout for things such as knob and tube electrical wiring, radiant heat, and the possibility of asbestos tiles particularly in the basement.

Other than I fly into the airport just n. of town and the one over at Courdelene   as well as the one up on the big lake north.. so I know it from the air  LOL.  

My parents are Air Force vets. :)

I'd look in areas such as The Village, Midwest city,  and Del City near Tinker Air Force base, and some areas near downtown.  

This area is great as there is a university and the Air Force base that will attract tenants, but you'll have to be patient to find the right deal. 

Per the seller, the property is a fixer upper, no central air or heat only window unit.

I'm currently employed as a welder at a local shipyard, and I also serve in the Air Force Reserve.I have always wanted to pursue a career in real estate, but honestly I was scared of the risk.

We installed central air and the bonus room, but never did any flooring (didn't need to).  

Just realized our garage could be a perfect 420 sq ft apartment that would rent for $800-1000 or we could get Air Bnb tenants all summer in there, either way would bring in about $10,000 per year.