City of chicago has all sort of rules about security deposits.

So you might get rent and deposit before first payment due....or as you suggested might have to make 1 or 2 payments before rent starts coming in. 

He hasn't responded yet, nor deposited the rent as of 3pm on 2nd.

In regards to a deposit, I am used to longer term rentals so in a short stay like this what is typical?

I cancelled the transaction and requested they sign a release of my deposit, (which was held at my attorney).

., odds and ends left in the house, no furniture), you can officially change the locks and take possession.Send a registered and regular mail letter to their last known address (your property) stating the abandonment and breaking of the lease, and keep the deposit.

"Loans Secured by Financial AssetsWhen a borrower uses his or her financial assets—life insurance policies, 401(k) accounts, individual retirement accounts, certificates of deposit, stocks, bonds, etc.

Also, i take a slightly higher refundable deposit.

I actually have to sign (as the agent) that I received that EM deposit.

Even thouse can be hard to get into without a good deposit.