Be sure to connect with the local REIA groups - and when you visit plan around their meetings to meet and connect with local people who might have some of those 200 doors you are looking for.

Just thinking ahead another step... if a cosigner doesn't meet the standards I've set forth (lack of income, subpar credit, etc.) would it make sense to move forward with two instead of three cosigners, or should I require that the student find a different cosigner? 

You could counter will longer terms, lower payments, but keeping your asking price intact (if that solution meets your needs, obviously).

Meet ups?

If they don't meet your rental criteria, don't rent to them!

This all done without ever meeting face to face.

Aldermen won't get you anywhere- you need a zoning attorney, +architect for all drawings, town meeting with all the neighbors and a variance, which, in Chicago = $$$

This is the best real estate investing website that you will find.I am an investor and a realtor in the New Orleans area and I have been a member of NOREIA for several years, although I have missed the last couple of meetings this year.

Would love to meet other like-minded people.  

I advise you to take a bunch of meetings, look at some maps, eventually hit up the spreadsheets and see what local Realtors are telling you until it all makes sense.