Maybe I can help...
BabyDoll -- I'm just about finished with the progression you're talking about.. at Peoria..
I've been in the Peoria unit for about 8 years now (all the things that Korgs & pkober said about the unit are absolutely right on..) I enlisted as a crew chief after high school, got my ratings while going to college, then interviewed & got a UPT slot. I'm now finished with UPT & just started C-130 initial qual at Little Rock, & should get spooled up flying back at Peoria this summer.. After reading the previous posts, here's some things I want to point out...
1. Peoria is a great way to go & the IL guard really helps pay for school.. But to be clear, the IL guard grants you a waiver for 8 semesters at any IL state school (university, junior college, doesn't matter.) However, they don't touch flight fees. Just to be clear, I'm going to say again, the Guard doesn't pay/waive flight fees. (I suppose this could have changedin the 2 years since I was in school, but I seriously doubt it... Better do some serious research.)
2. Potential for misconception -- People who join the ACTIVE DUTY military out of the state of IL for 4 years or more qualify for the Illinois Veterans Grant, which does the same state college tuition waiver, but this one covers flight fees... (So, to recap, active duty covers them, the guard does not). With that in mind, you may run into someone who IS in the guard and DID have their flight fees paid for, but these are usually folks who came to the guard out of active duty & it was their active duty time that made them elligible to have their flight fees paid.. Absolutely confusing, but I'd be happy to talk more, just pm me about it..
As far as the GI Bill goes, the Guard has a little bit different setup than active duty.. You do not have to pay into it ahead of time, and the amount you get depends upon which career field you enlist into. Once you get to school, you stop by the VA with paperwork from the guard & they activate your monthly GI payments that come in the form of cash for you to decide what to do with.. If you decide to use this to pay for flight fees, you certainly may, other people (myself included) really use it to pay for food/rent/bills while going to school. (Your drill pay will net about $130 early on & you'll spend a fair amount of that on food & gas on drill weekend, so be careful when budgeting your drill pay to cover your other monthly expenses.)
Again, it's cash funds & how you use it is your deal...
3. It is most certainly much easier to be selected for a UPT slot if you are prior flightcrew than prior maintenance. (For example, enlisting as a loadmaster vs. a crew chief) I was prior maintenance, but the year I interviewed I got lucky in that there happened not to be any enlisted aircrew members from our base interviewing at the same time. So, try to get on as a loadmaster as your first choice, crew cheif as second choice, then really any maintenance position as a third.
4. I just want to be sure you're familiar with the amount/type of training involved.. Crew chief school is about 6 months long, loadmaster school I think is longer, but I'm not really sure how much. Then get your degree asap, and interview for a UPT slot.. Then there's a pretty hefty waiting period to actually get a UPT class date, for me it was just over two years. (you can usually interview if in your senior/late junior year as long as you can document that graduation is pretty much guaranteed). AMS (commissioning) is six weeks long, then UPT is about a year long. Then C-130 initial qual for another six months, and then about a 90 day seasoning period back at Peoria.. Things can get pretty stretched out if classes aren't scheduled very well, but that's often up to the whim of goverment funding. Plan on about 2 years for pilot training.
5. Pilot training for Guard/Reserve folks is exactly the same as it is for active duty. If you do not have a private pilot license when you go to UPT, the military will pay for you to get one. (It's usually referred to as IFT) If you already have at least a private pilot license, they pay for nothing.
So, the underlying theme here is this... The guard is a great way to pay for school & the 182nd is an excellent organization, but it is highly unlikely that anyone will directly pay for your ratings. There's a bunch of other little things that I thought of when I first read this thread but these are the big hitters...
I have very recently done exactly what you're talking about & I'm happy to give any advice you might ask for. (and probably some that you didn't ask for!!)
Hope it helps,
FlyIllini