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.

Not sure if this has worked through but a winery that has been long on the market might be suffering from poor practices by the viticulturalist.

Dumb decision that I don't support, but I don't think 1 DUI should be a character killer.

Most S8 tenants have a history of bad decisions, often having convictions, evictions, bankruptcies, chargeoffs, collections, garnishments, etc.

But given my parenthetical statement, and this shows where perhaps you may have less experience in the STR world, for no valid reason, your preferred platform can make a unilateral, unfounded decision to ban you and there goes your business.Which brings me to my final point.  

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

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. 

The PM handles almost everything except the decision-making.Would it be rude or inappropriate if I communicated directly with the PM without involving my realtor?

Sounds like it makes sense for you to partner, I would suggest: spell out responsibilities very clearly, how you make decisions and most importantly: have a very clearly spelled out exit. 

Cashflow, ability to build a team, landlord tenant laws, price to rent ratio etc.......were all factors in the decision making process almost a decade ago.Now,  I wonder why your approach is an either or view?