When I was 17 I had an old Les Paul ($200.00), an old Tele ($350.00), a TV Junior ($500.00) a BF Bassman (150) and a SF Vibrolux (got for free with the Les Paul and put 200 into fixing it) and a USA Strat (500).
I also had a studio that I recorded local bands in. I had a Fostex R8 and a peavey board (that stuff was expensive back then).
All paid for by me.
When I was a kid I mowed lawns (3 lawns a week @ 20 each), delivered papers (60 a week) and did snow in the winters.
I kept 3 a week when I was in 3rd - 5th grade and saved the rest, I raised to 5 a week in junior high and then in high school got a job.
I never asked my dad for money and always pretty much bought the gear I wanted. My dad set up a mutual fund for me and would take my cash and send them a check every week for what I made.
I bought my first car (used BMW 320 - cost me $1000) out of that fund and also used it for spending money for my first couple years of college.
I met a kid a couple of years ago who was the son of one of my wife's work colleagues. He had been mowing lawns/shoveling snow, etc. since he was like 10 or 12 and he owned two vehicles that he bought with the money he had earned and saved over the years - a Mustang (not sure of year) and a 2003 Explorer. I was very impressed with this kid. He was 15 when I met him and couldn't even drive the vehicles he already owned...