Storage:
First things first, you have to find somewhere to store all your stuff. I have seen too many people trying to find storage locations at the last minute because they had forgotten to do so.
Tips:
Think ahead and look at pricing for storage places. There are many storage services that are specifically for college students and offer special discounts if you sign up earlier. They will usually have designated drop-off locations that are close to your residence.
Student groups also offer storage services. Last year, I used Penn Hawaii Club's storage service, and I just had to drop my stuff off at the corner of Hill. I also know some frats offer storage in their houses over the summer as well.
Be careful when trying to store un-boxable items, like a fan or a piece of furniture, because many locations may ask for extra. You might be better off trying to find a friend to store it for the summer, but ask ahead of time and not at the last minute.
Hoarding:
One problem that people face is that during the time they've lived in their place, they've accumulated too many things. If you're not careful, you may find yourself needing more than 10 boxes to store everything on move-out day.
Tips:
Prioritize what you need. You probably don't need those 10 free T-shirts and those shoes that you were saving for the “right occasion." Go through all of your stuff, and separate out what you never use. If you haven't touched something in a year, it should probably go.
Try selling your items to friends or online (Penn has the really useful “Free & For Sale" page), or you can donate items to charity! Penn usually has boxes and trucks around to assist with that.
Crowding:
The unfortunate consequence of living in a dorm is that there other people- a lot of other people. And during move-out days, everyone is trying to leave at the same time. This results in a lot of time waiting for elevators that may crash, waiting for carts to be checked back in, and waiting for your stress levels to come back down.
Tips:
If possible, AVOID ACTUAL MOVE-OUT DAY. If your exams end early, take advantage of it. Try moving out early in the morning when everyone is still getting over that exam hangover. You will have free reign over carts and elevators. Also, you can trying moving out most of your items beforehand, leaving only clothing and bedding to be moved out on the actual day.
If you're one of those unfortunate people to have an exam on the last day (may the Lord bless your soul), then try getting an extension! There are plenty of opportunities that need volunteers and allow for housing extensions.
Carts from hell:
Yes, we go to an Ivy League university, but all they can provide us with are giant boxes on moving dollies WHICH MAY NOT EVEN BE ATTACHED. This results in boxes toppling over, dollies hitting you repeatedly in the leg, and possible catastrophe while crossing the train tracks at 40th Street. I'm pretty sure I've sustained both physical and psychological damage from using those carts.
Tips:
Truth is, there's so little you can do here. But one thing you can do is ask a friend to help you with moving. The cart seems a lot less hell-bent to kill you once another person is assisting. Also, if you're very lucky, you can try to snag the few carts that are actually attached to their dollies. They make the whole moving process much less stressful. But if you can't manage that, at least make sure to position your box properly on the dolly before putting anything in. Seems like a small detail, but it makes a big difference.
And there you go. Follow these tips, and hopefully you'll have a better move-out than I did. Now excuse me while I go nurse my bruise-covered leg.