1. I brought a laptop, it was very helpful because my issued laptop had the blue screen of death for the first 2 weeks. Also, bring blank CD's to burn info on since you cant use a thumb drive on GOV comps (preferably the RE-writable kind).
*Get to Walmart when you get there and buy 2 reams of paper if you bring a printer, I also suggest bringing several cartridges of ink for your printer... you will be printing a lot of stuff for the entire flight if the printer in the building goes down (highly likely)...
2. You need 3 pairs of blues pants, don't worry about poly vs wool - they are all the same in the big picture - all that matters is that all three pants are the same blue color as your service dress coat. The supply folks should have given you blue pants that match the coat.
3. The insignia for officers DO NOT have circles, wear those & the silver braided (Officer) flight cap. Also - make sure you get with someone at your home unit that knows how to put a uniform together and have them help you put all the accouterments on the service dress coat (Im assuming you are non-prior, if not sorry...) and leave them that way. Try everything on before you go. As well, go through each garment and clip all the extra strings from them and check the pockets for inspections tags, it will save you a lot of time and hassle if you do this now. Since you are going in the winter I would bring a Gortex Jacket AND FLEECE LINER. If you unit wont issue you a gortex, thats ok they have them there to borrow, but not the liners. Buy the liner if you have to, its cold.
Lastly - When you get there read the "reg" that governs how your room has to be set up, particularly what HAS to be displayed in the room, and what does NOT. Take excess crap and put it in your / a flight mate's car until graduation. Have Fun, PM me if you have any other questions.