Just carpet and paint for two units that size will easilly be 10k and chances are you are going to need other work.

I already have one property in town that is about the same size and I'm using the insurance cost on this place.  

Baby Boomer are getting up in their years, many are down sizing, moving in with family and even passing on.

The basic acts of screening tenants, signing leases, paying the bills and receiving the rents are administrative in nature, and if in a modest amount would not likely be viewed as providing services. 

(We are confident in these numbers for rentals these size).

Hard money, HELOC on your primary (if this isn't your primary), friend and family loan, hell even CC depending on size and timeline of rehab/ sell or refi.

Hello,I'm wondering if anyone can recommend a good strategy for finding good off-market or non-MLS deal flow, particularly in the small-medium size multifamily space.

Illinois/Chicago has high property taxes compared to many mid-sized cities/metro areas. 

So if you're getting a Walmart size annual NOI and you're getting $12K - 18K in appreciation every year that's not so bad. 

No it's not a multi family home, however it does have a full size refrigerator, cupboards, microwave and sink (full wet bar) in the basement.