The more you know, the faster you can recognize opportunity.

Then it's buy buy buy Seems someone besides me recognizes the problems Chicago has created for itself.

Sponsors and investors that recognize that social and cultural conditions could also negatively affect their assumed 30% IRR would have a better chance of survival if and when the apartment bear market arrives.

I would also recommend interviewing the realtors in person. 

Interviewing the management team can be one of the most important steps you take when acquiring a large asset. 

Does anyone have their own template of best questions to ask when interviewing/vetting through Contractors, Project Managers, Hard money lenders and Agents?

This comes from several people we interviews completely unrelated.

Background is in dealership management, nationally recognized, so I'm great at closing/negotiating, numbers, and navigating a deal, and I'm naturally more transactional inclined. 

Interview a couple and make sure you pick one that has a good network on the ground and it looks like you are leaning that way so that's a great start.

You can do that by stating base requirements up front; phone interview, do some online checking-facebook etc.