PLEBE SUMMER:
Try to drop off your first care package the day before or the morning of I-Day.
I highly recommend the individual packs of drink mix that can be poured into water bottles. The water in Annapolis tastes like crap in general, but the old pipes at the academy are especially bad about leaching into the water. I really liked Propel because it tastes good and it mixes clear so it can't stain your White Works like Gatorade can.
Send shout wipes, you get issued some but it's always good to have more. I found Tide pens to be almost completely worthless compared to shout wipes or bleach pens.
Chafing can be a problem that gold bond can't always solve, I liked having body glide for that.
Clif bars, powerbars, and the like are awesome to get. Don't forget about homemade cookies.
I grew to appreciate having magic erasers, swiffer dusters, and various kinds of tape (duct, masking, packing). They all made cleaning and moving easier.
AC YEAR:
Make sure you don't have a crappy cell phone that doesn't have media and email capabilities, you will thank yourself later in the AC Year when you can play games in some down time to unwind and you were able to get emails on the go without being back at your computer (chopping up stairs to check your email really blows). My roommate almost got fried earlier this year for not doing something in response to an email he received while at class and didn't read until it was almost too late.
COOKIES ARE ALWAYS WELCOME!!!!!!!!!!!!!!!
Look into getting magazine subscriptions. I get Scientific American, Time, The New Yorker, and the Atlantic Monthly delivered to my PO Box at the post office. You don't always have the time to read everything but it is important to stay informed and it gives a good source for the current events articles that you will rate knowing as a plebe.
PRINTER: You will probably want to just get a printer on PPW, you can either get one at staples or officemax in Annapolis or you cant buy a printer at the Midstore.
There isn't much that you need from home that you can't buy from the Midstore, I highly recommend such conveniences as...
a.) An electric razor, they are great time savers in the mornings. Personal preference here, this is the one I own and it works great.
http://www.amazon.com/Panasonic-ES8...MY9Q/ref=sr_1_2?ie=UTF8&qid=1304316364&sr=8-2
b.) A small clip on fan for the cubbiehole above your rack such as this one,
http://www.amazon.com/Holmes-HACP7B...P4WO/ref=sr_1_1?ie=UTF8&qid=1304315215&sr=8-1
c.)Your own personal pillow, the issued ones suck and offer almost no support. I've grown quite fond of my brookstone memory foam pillow, during the ac year you really don't have to worry about upperclass taking that stuff away b/c they understand how important sleep is and that you should be doing whatever you can to get as much sleep as possible in during the hours you are allowed to be in your rack (2200-0630).
d.) Going along with that, I also recommend getting a sleep mask. You will be living in a room with at least 2 other people who will likely being doing things at different times of the night. Make sure their work doesn't interfere with sleeping. I like this one
http://www.amazon.com/Revolutionary...Z6FK/ref=sr_1_6?ie=UTF8&qid=1304315847&sr=8-6
f.) Something to consider a little ways down the line is to get a second monitor, it is very common here to have more than one connected to your computer. I got my second after Christmas and it has been awesome. It makes doing much of the computer based homework we do here less cumbersome and time consuming. I got a good deal on newegg, check there.
http://www.newegg.com/Product/Product.aspx?Item=N82E16824009255
g.) For Christmas I asked for a good multitool, they are very handy to have around due to their versatility.