Hypercarfanatic;
As an A&P for the love of god don't be that pilot.
DON'T TURN INTO THAT PILOT!
-A Grumpy Mechanic.
As for flight schools, pay as you go. Go Wally's route if you can. Don't get into one of those 4 year programs. If you want to fly passengers expect to log at
least 1500 hours for the ATP rating. You need one to be considered by many regional carriers. My company just dropped it's requirement since the pool is damn near dry for pilots willing to work for $20/hr.
Getting into a mainline airline won't happen unless you know someone on the inside. Nepotism -er 'Networking' runs rampant in the industry, unfortunately.
As far as cheap useful headsets: Softcomm C-60. I have 4 sitting that need repair and I fixed the 5th one and it ran me $80 shipped to be fixed from a hunk of plastic. Softcomm is US made too, small outfit out of Arizona. Between $150-180 new for the C-60 model. If you want one I could set you up since they're only sitting around in my closet.