If I had it to do over again...(wouldn't that be nice:-))
Apply to service academies (AF/Navy probably gives you a better chance of flying, WestPoint seems to set males toward the Infantry/Armor/Field Artillery track, although they do send some people to Flight School).
If that opportunity does not materialize, enlist in the Air Guard/AF Reserve at 18. Get into maintenance or something else where I would have interaction with Flight Crews. Use the GI Bill to go to a good college and get a degree in something OTHER than aviation (although as some have said, aerospace engineering is a good field.) Shell out the money for a Private Pilots license on the side.
After college, use the network established in the Guard/Reserve unit to apply for a flight slot. If all works out, the military pays for all your ratings (except PPL), and a college degree.
PM me if you have more questions