Collecting 1st mo. rent, last mo. rent, and security dep?

[Douglas T.]

Every apartment I've ever rented has required me to pay 1st mo. rent, last mo. rent, and a security deposit equal to the mo. rent.... so 3 mo. worth of rent payments upfront. I'm now using a property manager to find a renter for my Chicago condo. He's telling me that it's unusual to collect last mo. rent upfront and asking if I'd take that requirement away. Several property managers in Chicago all explained that Illinois laws favor tenants in cases of landlords keeping security deposits for damage done to the unit. Landlords rarely, if ever, win and get to keep part of the deposit. Because of this, landlords in Chicago are moving toward non-refundable move-in fees. I'm charging a $350 non-refundable move-in fee and my HOA charges a non-refundable $250 move-in fee. So, I'm not even asking for 3 total mo. in rent up front. I'm only asking for 2.5, in fact. Am I missing something here? He's asking me to take away my move- fee... which leaves me with nothing if damage is done to the unit. Or he's asking that I not ask for last month's rent... which also leaves me unprotected at all if this tenant decides to move out in the middle of the night. Any thoughts on this?