Do you anticipate a 3-4 month rehab period prior to listing?

As long as your on the list you're good as long as you follow the same rules as everyone else. 

I didn’t get the listing and commission.

For those of you who have done direct mail marketing to multifamily owners (5-35 units) how many properties is a good number of properties to have on your list before mailing? 

The same listing can go from a great cash flow on day one to negative cash flow based on how the buyer plans to finance it (conventional investor loan with 25% down, FHA 3% down house hacker, cash, etc).

I would love to meet up with active Real Estate Investors in the Chicagoland area/surrounding suburbs to pick your brain a bit, possibly shadow you on day-to-day activities, and see how to successfully go about beginning on this path to wealth through Real Estate. 

Nobody has a crystal ball but Grays Ferry is the most depressed of the markets you listed and therefore could theoretically appreciate the most if the neighborhood turns.

We truly believe Jacksonville is next on the list as those three cities have become very populated and expensive.

The list of potential benefits is endless. 

I have a lead who i offered a subto/seller finance option to. back story lead is getting a divorce and can get ~340k if listed. asked 300k if sold to me, everything updated within past 5 yrs except carpet and interior paint.