It's really just the lost deposits that are the biggest unknown and could make or break the deal. We have notoriously bad luck with getting dinged for extravagant crap off our deposit no matter how spotless we leave it. $75 cleaning lint from behind the dryer, $75 oil cleaning of range hood, $50 wrong touchup paint color that was given to us by landlord... I could go on and on. I don't believe we have ever lost a full months rent worth of deposit though so maybe I'm overestimating. I tend to assume the worst about everything.
Seriously, every time there is crap I couldn't predict in a million years. So its hard to say how much we would lose. All of it, maybe not. But according to yelp reviews of my management company it could be a lot. We did take a ton of pictures, but the place is old and started with a lot of questionable things they could try to ding us for that either happened while we were living there or were present before but weren't noticed for awhile. Although I always go through the effort of demanding mailed letters, phone calls, and emails I'm really not prepared to go to court to fight for my money.
Plus the non-$ portion of actually moving everything and resetting it up again. Yes, we have a ton of crap. And packing/unpacking/organizing is pretty much all on my shoulders. We always end up breaking at least 1-2 items of varying value. There's always the money spent switching out furniture that doesn't fit.
New place is $200 a month cheaper, better layout, more updated, but worse part of town. It is available 3/5 and our lease is through 3/31 so I'd expect to pay at least double rent for two weeks. The interesting part is we might be planning a trip for the last two weeks of March. So we would be paying double rent while not even in town... I love where we live but feel guilty about how much we pay. The best part is living downtown, but last year when DH lost his job, rent and utilities was more than 50% of my pay so we couldn't even spend money going out!