Here's a link to the data: https://mred.stats.10kresearch.com/infoserv/s-v1/vwxv-Zs5What this data shows at a Macro level is that the Chicago market is doing fine, but the market is too large to use that data to make any decisions about where you want to house hack.

I am not going to move into a dormitory style house and raise my two year old in a location with poor schools and incredibly dense housing, unless I have no other option. 

I seem to remember that I didn't even have a business card until then either.You are VERY late to the game to be making these decisions. 

It is the seller's decision to sign or not.  

What information I should be analyzing to help me make a decision on where I should start.  

Turned a single family house that was poorly marketed but in a great area of my city, listed mid-winter where there's less competition, into a duplex for all intensive purposes and used airbnb to rent out rooms.

Point being that property you acquire 1-2 years ago is likely to be subject to deferred maintenance and capex, so their "long term" performance in rankings 1), 3) might skew poorly in year 1-2 but may pickup  after you've found and fixed all the hidden issues.I know if i did this exercise across my portfolio, the recently acquired ones wouldn't be fairly "stacked" because of all the year 1-2 cost build up from what the seller deferred, but have good chances at being future performers in years 3-5.Maybe that's why you have 2) and 5) but curious your general thoughts here are for evaluating this. 

Or like some of the crowdfunders money flooded in and they made some pretty seriously poor lending choices and they themselves and their investors got wiped out.

We built it out of necessity and started same way as everyone, cut our teeth on bad decisions.

It's cool to know how to use tools to a do analysis but it has to be utilized properly.I have seen several flippers who have read Rich Dad Poor Dad; had every Performa, chart, analysis package, market analysis reports, cost benefit analysis, work break down structures, IMS and much more and botched every project.