The house would need pretty extensive upgrades -  I would need to replace entire HVAC system (including converting from oil heat to gas) and it would most likely need roof and siding. 

At that time I had about $90,000 in an old retirement account from a previous employer which I converted into a Solo 401k with the intent of loaning myself the necessary money to complete my first rehab project.  

The house is a converted SFR, turned into a duplex, with converted garage, making it a Triplex basically..The county (Jackson county, Kansas city, MO) is still showing SFR in public records.

Converted the floors into condos and sold the top two floor for $500k a piece and than the bottom triplex for $1.5M to my friend.

I represent a real estate lawyer that is interested in getting into convertible living solutions in chicago.

It is a flat-topped mesa on the north side of town that used to be farmland with a few view mansions on the edges, and has been recently converted to high-priced SFRs, and is a popular place to buy vacant land and get a cookie cutter SFR built to live in.

I am completely uneducated when it comes to what is needed to be known about being able to convert this to multi-family units.As noted, it is in a historic District so I am assuming like most historic districts, the outside would have to remain the same (which wouldnt be a problem).

The grand hall still had most of its gas light fixtures which had been converted to electric.The original kitchen on the back of the house and the servants quarters above have been converted into an 2-bedroom apartment (I would guess back in the 40s based upon the age of the appliances - there's a 1930s/40s electric range which is in like-new condition).Similarly, the gardener's quarters in the walk-out basement has been turned into a 1-bedroom apartment - probably in the 1950s. 

Maybe finding a house and converting it?

I would really appreciate feedback on this deal.SFR, 1939 sq ft, 7400sq ft lotCurrently a 2/2, I plan to convert to a 3/1 plus efficiency.