.: I invest out of state in C-class neighborhoods in the Midwest.

Which will also depend on the neighborhood.You want to, "rehab/maintain to the Neighborhood".Most investors go overboard on their first rehab and waste a decent amount of money.

My opinion is a lack of business organization.

Look at recently sold properties in the same neighborhood that match the size, condition, and style your property will have post-rehab.

For example, intro's to people here that can help you with certain specialties, planning, feedback on neighborhoods, financing of course, etc.

Start by exploring books, YouTube channels, market research, and analyzing trends in neighborhoods.

If you haven't already, try going off market, driving around neighborhoods that would be of interest to you and finding ones that fall into your criteria (your agent should be able to help you as well).

But this comes with pockets of C/D neighborhoods, and higher potential for headaches;  in addition, appreciation in these zips has probably maxed out for a while.

My vision is for this meetup to be informal and organic.

What neighborhood of Chicago and how large are the buildings?