9600 pro [~$100 '04]
X800XT AIW [~$300 '05]
8800GTS-320 [~$250 '07]
8800GT-512 (went through 2 of these...killed the 1st 1 w/ a bad HR03-GT mount and lots of voltage) [$200 '07]
8800GTS-512 (went through at least 3 of these before getting one w/ Samsung RAM that I wanted) [~$160-$360 '08]
4850-512 (bought 2 for X-fire, but 1 got lost in the mail...decided 1 volt-modded 4850 was good enough for 1680x1050 and I eventually was reimbursed by the USPS) [~$150 '08]
GTX280 (wanted a little more power for 1920x1200, and the price was right...classifieds) [$250 '09]
After I built my first PC (P4-2.4A) while in college I was eager to upgrade soon. The next year when I started working I sold that one, and moved up a notch (P4-3.0E). After that I had a bit of a lull and only did minor upgrades...mainly peripherals. Then once I got married a couple years later I started to get more serious about this hobby. Got a Q6600 rig, started volt-modding stuff, and never looked back!
The only card I really regret purchasing was the 8800GTS-512 on launch day at $360. When the 8800GT came out it actually went up in value for a little while, and I thought something similar might happen w/ the GTS. I also thought I bought the version that came w/ Crysis, but it did not. The 8800GTS is an awesome card, but it rapidly decreased in value. Now I wait, and buy used if I can.
I voted every year, and $200-$300.