Andrew, you still seem to be laboring under the misconception that everything in the Navy makes sense- FTR, it often doesn't. You can NOT have those extra items in your possession when you leave Great Lakes. End of story. They can be mailed to you once you arrive at Goose Creek. Ease back a little on trying to push the edges. Good luck. 
Im not under any misconceptions...thus why I asked the questions to begin with.
And me and spending money...yeah, I actually hate doing it--When I signed my contract with my bonus amount...I was like "alright, cool--not like im going to be able to spend it on anything"
I wouldnt really consider myself A biker...more like Im cheap and dont want to pay for gas! When I went to my university, instead of driving all over campus (which was a pain the the A** stupid one way streets...turn abouts, the street system was planned by a north korean nuclear bomb maker i think...) I just rode my bike from one building to another. What will my itinerary look like through the pipeline?? Will I be pretty much in the same general area all day for classes?
As far as wearing civies goes...I could honestly care less. The tech school I went to was uniform code--as well as work. I practically slept in steel toed boots and dickies.
Charleston has been our families vacation spot for many many years now. We have family and friends that live there as well as in Hilton Head--Its a beautiful area with Asheville being only 4 hours away.
In all honesty, will I even have time to go out and hit the paintball fields?? (im a big baller...suppose ill have to use field gear?) and played varsity golf all through school.