No worries. I figured you were retired military. Nothing I've said is really "top secret" but I just thought it would be a good idea to ask
I would play a wait and see until you get to class. You really won't need the stuff on day one and you'll have a pretty good sampling of people to quiz about preferences. Your airline may also have specifics about bag size. I know a 22" bag will fit in every overhead with the exception of CRJ/ERJs.
Personally, I can't justify spending a ton of money on the luggage. I did buy a little nicer than rollaboard from sears and a catalog case from office max but there are some seriously expensive bags out there.
http://www.outermarker.com
http://www.stopoverstore.com
I have purchased from both stores with good results. I'm partial to outermarker because I know the owner. He owned a shop in STL while I was doing my training and there were many times I was looking to spend money on crap I didn't need and rather than taking my money he told me to put a product back on the shelve.