I can't speak to how long getting the building approved by CHA takes, as mine was already approved when I had purchased it, but the individual unit inspection typically takes less than an hour.

Individually we can do nothing but continue to try to out bin eachother on each offer.

If they are friends, roommates, dating, or whatever, then I have minimum qualification standards that each individual must meet.

Each room has individual controls .

Most people would list and sell them individually because an owner occupant will often pay more than an investor. 

Yes, I had always heard that it could be hard to finance a property outright with an LLC, so I'd always assumed it would have to be done in an individual's name first and then transferred to an LLC afterwards.

Is it individuals or companies?

If none of that was done, you just made a $50 voluntary donation to someone....I suspect it will be a matter of time until the individual that received your "donation" receives a visit from the FBI for wire fraud. 

These costs for most of the individuals are considered personal in nature( unless you have RE portfolio that is run like a business- see below).

I am new investor in Chicago looking to connect with other like minded individuals.