1) In order to be a pilot in the military, you have to be an officer. In order to be an officer, you have to have a 4 year degree. That said, many airforce bases have flying clubs with training at a reduced rate from the standard flight school. Or, go to school and do the reserves, or ROTC while working on your degree and maybe pick up a couple ratings on the side.
2) Read the fourms here. This might be one of the most unstable career choices you could make. The only sure thing right now seems to be WN, FX, or 5X.
3) Captain upgrades depend on the airline. Most regionals vary from one to five years. The latter ones typically pay better or have better bennefits. There are basically two types. Fast upgrade, crappy pay or slow upgrade, ok pay. Most Majors aren't hiring and won't be for some time. Look at the pay section of this website, many of the airlines show the junior captain's hire date. If it's 1990 you can expect 15 years as an FO.
4) Budget about $30-45k for your ratings from private through CFI.
5) First year FO, at most regionals will put you near poverty level. Yeah, $19 an hour sounds great, until you figure out that you're only paid in block time. The time at the gate doesn't count. By the time you put in that 13 hour day to fly for 6 or 7 hours you're making about $6 per hour.
6) Read some of the other fourms. There's one about "out and backs" that gives some good insight.
7) You should always do your best in school(thanks mom!). That being said this is often an industry of who you know, not what you know. Assuming you're not a total idiot it's a pretty level playing field. We all have basically the same skills in terms of airmanship, and experience when we get hired. What sets you apart is the person you are and the people you may know.
8) UA recently liquidated the employee pension fund because it could not make payments on it. DL and NW are thought to follow suit. What has this taught me? First, don't rely on one source for retirement. Diversify so that if one does bad, the other picks up the slack. Second, don't live outside your means. If you're making 100,000 per year but spending like you're making 200,000 you're in serious trouble when you get that furlough.
A little background on me. I recently graduated with my BS. I'm finishing up my CFI and currently have about 300 hours. I started flying because of interest I have in aircraft, not the money people thing pilots make. In the five years I've been flying I saw people getting on at regionals with 500tt, upgrading in a year and flying for a major less than 5 years after they graduated. Things changed after 9-11 and they haven't quite stabilized. Fuel costs, war, media hype (SARS) and stupid management have caused a lot of turmoil in the industry. It's constantly changing. What is put here by myself, or any of the much more qualified members may not hold an ounce of truth 5-10 years from now when you have the experience to get hired.
I think the military is a great option for some people. I looked at it and after a lot of consideration decided it wasn't the route for me. Don't do it (or anything for that matter) because it seems like the fast way, the easy way, or the way that everybody else does it. You're 16. You have two years before you decided to go to school, or go to boot camp. Regardless of which way you go, I would go to school first and join an ROTC program. They'll pay for some of your education and life as an officer is better. Regardless, research as much as you can. Don't just listen to what the recruiters have to say (even college). Talk to people that know first hand. Get the real take.
Regardless of what you do, don't go somewhere that makes you pay for a job, like Gulfstream Academy or Delta Academy. It may be the easy way, but you're only hurting your cause in the long run and costing yourself a lot of money.