I know nothing about this 10 to 25 unit market but I have to chuckle at the logic of the standard, Illinois is crap, responses.Taxes, rules, laws, regulations, population decline, state/local financial strength....any of these commonly cited Illinois/Chicago "issues" are baked into the price and the deal.If it were actually the case that these issues made Illinois property less attractive, then you would actually find what appear to be MORE deals because demand to own property would be weak.

Each has strengths and weaknesses.

@Chase Cline Another idea that I came across in the book "Real Estate Loopholes" by Kennedy and Sutton, says "if you hold real estate in a state with weak or non-existent charging order remedies, you may want to consider using two LLC's for protection."

The Salesman has lots of templates, one of which will surely fit you.2)  The attorney honestly addresses issues and presents both weaknesses and strengths of a structure. 

If this is helpful to anyone reading- I vet deals for PMLs now and charge $200 to underwrite their deal, discuss the weak points I see, discuss contract recommendations, suggest verbage to consider, and ultimately help PMLs have a clearer understanding of the level of risk their deal involves.

Surround yourself with people who are strong in areas where you are weak.

I knew the business, I knew how to flip a house, but some of the things I was hearing was starting to point out all of my flaws and weak spots.By day 3, I was ready.

Your greatest strength is your greatest weakness!

If it was much larger though, I'd certainly look at my weaknesses and offload that ASAP.

and we hit a lot of struggles/hurdles/failures and we just keep getting back up 2. have great friends, mentors, consultants who have helped us see where we're weak, and help us course correct when needed, lift us up when needed, etc."