I'd also like to echo the sentiment of others in saying that it would be better if you just invest in a REIT or CD (chosen based on your appetite for risk) until you're back...BUT, and this is a big BUT, I feel that instead of investing money over the next 3 months, you should invest your time into learning about REI & read books that will help give you a great confidence boost and "success mentality".

If the seller in fact fixes everything....even replacing the roof....and I've done full due diligence on the other components involved (neighborhood, market, numbers, PM (or chosen my own PM)), then why would I care about the seller himself? 

Whether this is an acceptable risk depends on your financial situation, long-term goals, how leveraged you intend to be, and your chosen risk profile.  

Our family friend and mentor we've chosen to work with are very knowledgeable with negotiating real estate and willing to work with us and help us out.

Vett your chosen lender and because you are dealing with a direct lender and not a broker and yiu should be good.  

Otherwise, factor those into your offer.Re: the bureaucracy, I think that's a factor in choosing where to invest, but if you've chosen Chicago to invest in already, I don't think the bureaucracy in this case is going to be that much worse than normal for Chicago.

I think ANY investor should take the licensing course in their chosen state as you will garner a ton of valuable information....plus start networking as that's going to be a huge part of your success or failure.  

The last thing you want is to walk into a deal where you have a bigger liability that you would had you chosen to continue to rent you space.In my advisory business I don't know why more doctors (and other small business owners) don't buy their own office buildings and rent out space to tenants and have them pay their building expenses and mortgage - makes all the sense in the world right.  

You have chosen a very challenging area. 

Another aspect is the availability of fractional financing under conventional loan guidelines, a TIC owner may sell and finance their interests as a conventional residence, like a condo loan, staying out of commercial lending requirements.Unlike other joint tenancy forms of ownership, a TIC owner may leave their estate to chosen beneficiaries instead of other owners.