Here's my progression:
Age 15: spent $300 and got a CB percussion 5-piece. Yes, it was as sweet as it sounded. It came with a crappy hi-hat and cymbal stand, and a Zildjian Scimitar crash and hi-hat set. Which sounded like a pile of scrap metal being dropped off a 10 story building. Over time, I got a Pearl eliminator double-pedal, some Paiste Alpha cymbals (and a Sound Formula crash), and was a happy high-schooler.
Age 20: got some money from an inheritence and bought a Pearl export series kit and a used DW maple snare. Sold my CB percussion set (w/ Gretch snare) for $400. It was like stealing, but the guy made me an offer and I took it.
Over time, I replaced the Pearl pedal with a DW 5000 pedal, got all new hardware (stands, throne, etc.) and built a complete lineup of Sabian AA/AAX. I owned that kit for 10 years, and never will have a bad thing to say about it.
Age 30: ponied up and got a DW maple shell kit (10, 12, 14, 22) in burnt-toast fade, and a Pearl Icon Rack (Gibraltar tom mounts). I think I'm finally done building. I slapped Evans Genera G2 clears on the toms (my favorite batter) and an Evans EQ3 kick batter, and I could not be happier with the sound. The 10 inch tom just sings.