Have you asked your new landlord how much time he’ll need to make the “necessary preparations” that he’s legally obligated to make? Maybe he’s already got a plan in place. Maybe he doesn’t and a friendly phone call will remind him that he’d better get on the stick.
Then, if his timeframe doesn’t fit with yours, ask him what he intends to do about the fact that you won’t be able to move in on the agreed-upon-and-paid-for date. You should be able to work something out.
You know, there’s a point. Most apt building have some sort of storage area, maybe you could unload into one, and just take the mattress and dishes upstairs until they’re done?
Okay, so current landlord is fine with me moving out first thing Sunday a.m. (yay!) and won’t even charge me for the day if I’m out before 10, which I will be. New landlord assures me the place will be cleaned and painted for my arrival, which we’ll see about. Apparently this isn’t their first rodeo (that wasn’t his exact wording, but he made me feel like an ass for asking) and they’re equipped to prepare units for first of the month move-ins that were occupied until the end of the previous month.
Okay. I feel a little better.
Did you talk to the new landlord about the odds that the old tenant would hold over?
You are not an ass for asking him about this. It’s a perfectly reasonable question given the dates and times involved. Don’t let him intimidate you for asking basic questions. He might have been to a lot of rodeos but that might be because he’s a clown.
So, which apartment did you pick? The one with or without the laundry facilities?
He wasn’t a bully about it, but he somehow seemed miffed that someone would question whether or not the unit could be turned around to move-in condition within 24 hours. First I asked if the apt would be ready for me considering the tenants won’t be out until the previous day, and he said yes. When I asked what would happen if, for whatever reason, it wasn’t ready he assured me that a) it would be (this is when the rodeo bit came up), and b) if not, he’d give me my money back for any day(s) that the place wasn’t ready for me to live in.
Renee, neither. I picked a separate apartment entirely that was pretty much exactly what I wanted.
Welcome to Chicago!
The move in-move out dance is pretty much SOP here. The property managers usually have crews on hand to turn the apartments in a matter of hours if there is no major damage/cleanly needed.
I didn’t realize you were moving to Chicago! Hon, I’ve got a comfy sofa if you need it. There’s probably an air mattress around here if you’d prefer it. Honestly. North side, about 30-45 minutes to downtown by bus and train. PM me if you need it.
Give me a couple of weeks to finish up school, and you to settle in a bit, and maybe we can talk the Dopers into a ChiDopefest to welcome you to town in Doper style. 
I’d be down with that too (assuming scheduling works out, it done exploded recently).