My wife has strong managerial and book-keeping skills and could likely handle GCs quite well.

Im looking for some information regarding the following.Every market has their obstacles and challenges.

I personally think that Rent Control will literally kill the city's rental market as well as force investors to look elsewhere thanks to the fact that Chicago is already a challenging place to be a landlord. 

Another thing, I think how you handle pre-screening and having tenants pay for applications is market dependent.

How do you guys handle investment properties and spouses?

I have plans to do wholesale transactions but will use and trustee to handle those transactions. 

I have conservatively valued and suggested a sale price of $160K-$165K based on increased values the past 3 years coupled with the challenging location and current condition.One of the neighboring businesses is interested and threw out the possibility of seller financing.

Each step has its own set of challenges. 

Challenges?

Trouble is, people mistake for a transactional business.So the best way to take down a deal such as this is to build up your network and relationships before you score a deal bigger than you can handle.