However I have heard mix things about me listing my own flip.

I'm a little unclear on the question.An HOA should have an insurance policy package that covers the general building, common areas, general liability, directors & officers coverage, worker's comp, and a mix of other things like non-hired auto and perhaps region specific things like flood or earthquake coverage. 

North Lawndale isnt hot area especially for a mixed use those are practically being given away free if they need work. 

The street has a mix of multi units and single family so I am not sure why the town would disagree but I have never been through the process so that is complete speculation. 

Yes, I know that there are a few bad ones in the mix.

Hi, I am developing a mixed-use property with 9 residential units (about 1000 sq ft each) and 1 commercial (1,600 sq ft first floor and 1600 basement).

Hi, I have a new mixed-use property with 9 residential units and 1 first-floor commercial unit.

There are still plenty of areas near downtown that are just starting to see new builds pop up, rehabs taking place, mixed use commercial widening, etc.

That those are my 2 options.Another quick question to throw in the mix...can you Fix n Flip or BRRRR with a 3.5% FHA Loan and not 20% down?

A specific niche to apartment investing is "value add" where you could be in the mix of apartment investing well before 10 years - Jake and Gino's Wheelbarrow Profits is a great book to learn about the concepts of this process.