Here's what I would do
I will attempt to answer some, but not all of your questions, but realize that I have been out of the loop for some time. There are others here who can chime in with the most current trends.
Here goes:
For starters in your case, here's the 136th AW in the Texas Air Guard's website contacts. Give them a call yourself and create a path. Go visit them. Find out who the unit commander and the director of flight operations is. If your first contact is a recruiter, don't discount what they have to offer as you may be interacting with them later anyway.(See below):
http://www.tx.ang.af.mil/136/unitinfo.htm/directory.htm
1) OK- You are obtaining your Private Pilot's license. That MAY give you the edge amongst other candidates, but realize that your skills will be screened down the road (At Hondo Texas, a subcontractor once provided screening of applicants in the Cessna T-43- a 210 HP C-172) Your private license may be ink on a card, but that's it when your skills are assessed. You will not need alot of hours- just keep up your currency and maybe add an instrument rating if time allows.
2) This has worked in many, many cases AND your enlisted peers will respect you better when you have to work along side them as an officer later. Trust me on that one. Think what it is like when someone off the street slides into a AMS/UPT slot, that hardly anyone or no one in the organization personally knows? How would you feel in looking at that person?
Here's the long route. If you are looking for a short route (instant gratification), it probably does'nt exist. Enlist in the unit you want to target flying for, go to basic training ASAP with an open career field selected that should put you interacting with flight crews. Now that is a good all around way to open the door to subsequent actions, such as taking the AFOQT, applying for AMS/UPT, etc. Basic is about 6 weeks at Lackland. Tech school for your career field (say loadmaster) could be OJT (On the job training) at your unit or a few weeks up to several months like my training in flight simulators.
You can get yourself a full time job in the computer field when you get back and attend your guard driils on weekend and 15 active duty days per year while waiting for a AMS/UPT slot. The advantage of the guard and reserves is being able to have a full time career or own a business while flying weekends and the yearly active duty.
The whole AMS/UPT time frame depends on budgeted slots by fiscal year and who is in front of you, as well as those competing against you. It can take 1 year, or it can take longer. If your unit prospects are slow, then research what is going on in another unit or another state's unit. Don't confine yourself to C-130's or KC-135's or whatever at this point, because you will short list your options. Your options MAY be shortlisted at UPT. Don't do it on your own early in the game.
3) Class 1 medical- You should not need this, unless you are wanting a reading on your applicability to that standard as compared to the entry requirements for UPT. You will receive a battery of physicals prior to AMS/UPT to confirm your eligibility.
4) AMS/UPT training beginning to end- 6 week AMS, then maybe a wait for UPT slot, then 49 weeks UPT, then advanced training in the aircraft your unit flies.
Hope this helps.
