Hey,
Excellent advice from all posters. I would like to second CCDiscoB's comments about staying away from the recruiters. THe only recruiter type you need to be talking to is a ANG or AFRES recruiter that is assigned to the unit you are interested in. There are active duty folks that are qualified to recruit for the guard and reserves, but their bread is buttered by someone else, and they MAY not have your best interests at heart.
Taking an enlisted position in the unit is an excellent way to get a foot in the door. I can't speak for all guard units, but when I went to NCO leadership school in Knoxville, I made friends with several of my classmates who were recruiters. According to these folks, many units will not hire off the street if they have sufficent qualified apllicants from within. Like you say, it is a bit risky, but hey, worst case scenario is you do a couple of interesting years as an enlisted dude, (I did nine) work on your certificates , and still be competitive for all sorts of flying jobs.
Something we often tend to forget in our mad dash to "success" is this: It's not just the destination dude, it's the journey too. Each of us brings our own perspective and background to the cockpit, making it a MUCH more interesting place. While I missed out on the opportunity to be humbled by the T-38, or throw my hat into the air on gradution day at Colorado Springs, I did get to teach pilots ito fly in 60 year-old rag & tube taildraggers, march troops onto the lawn of the White House many times and fly Learjets all over the world. Aviation is a blast because we get to share flying with folks who had different experiences than our own.
I'll get of my soapbox now. Braidkid, do not give up on going to UPT. Don't take NO for an answer. Befriend everyone you can in that reserve unit. Sooner or later, you'll find a mentor willing to help you accomplish your goals. Maybe someday we'll share a cockpit and you can tell me what it was like to work for Boeing.
DO NOT TAKE NO FOR AN ANSWER.
Cheers,
DAN