Dude,

You are doing the right thing by taking the initiative and thinking about your future now vs. the day after your enlistment is up. That alone puts you ahead of many. I would encourage you to explore going guard very seriously. Get your package/resume/letters of rec started now, schedule your AFOQT if you haven't already, etc. Get your package together and send it out to every guard/reserve unit that interests you. Phone calls to units don't hurt either. In the meantime continue flying on your own dime like you say you are - that shows a lot. You'll hear back from somebody, probably several units - go and interview. If you want this you have to go get it, nobody is gonna hand it to your on platter. I was prior enlisted for 5 years, and was lucky enough to get picked up by the same unit I was already a member of. It's been over 6 years since I finished UPT and I have worked as much or as little as I've wanted to since then. (haven't missed a pay day). I'm lucky to be in a unit where all the deployments are voluntary unless they need to be made involunary (not enough guys volunteering and that is never the case). PM me if you have any questions for me,...as I could go on and on about how good of a deal the guard is.