Find a park a distressed park, find some distressed trailers, put your husband to work. 

Buy something close to parks, nature, trails, or outdoor venues.

A couple other neighborhoods I like besides the two you mentioned are Washington Park, Hyde Park, Woodlawn, and South Shore.I think that area will continue to be gentrified because you have the lakefront as well as CTA trains.Is there any reason you are targeting Chicago instead ofdoubling down in Kansas City?

To provide a practical example, I acquired a 60,000 SF assemblage that contained an autobody garage, nearly an acre of surface parking and a 4 unit building in Philadelphia.

Best bet is likely (not absolute - everyone's situation is different) is to look at a national lender or broker that has options in lots of states - its a great development versus 20 odd years ago, with technology, internet, places like this - can have access to many more options than before (local broker or lender thats it)

(the Pier or Vinoy Park.. watch dolphin swimming in the bay while running/walking or just hanging out in a hammock between palm trees) . 

Looking for guidance on options. new builds aren't hard to finance and I would argue they are preferred to existing fix and flip loans, especially if you have experience. banks look at your experience, your builder's experience, loan structure, permits, etc you need to get an experienced builder familiar with advanced underwriting and negotiations with local, regional, and national lenders. in columbus we do ground up construction for clients at a 20% discount so they can BRRRR out of the new build with equity and we have pages and pages of data on what we build and why and it's all supported by market statistics. 

Just remember, you can't close on the replacement property before selling your current one.Qualified Intermediary RecommendationsFor intermediaries, I'd recommend starting with some highly-rated national firms.

Parking will likely be your biggest hurdle.

WE did a nice flip last may though in Winter Park that was a good one.