No the Drusin never gets like super amazing upgrades because I always get the latest stuff. I built a 3kish computer last year that i'm giving to my wife now and i'm building myself a new one. I just love building
I have a few upgrades that have been potent. Restricting it to computer only, I'd probably go ahead saying it was going from a mid-tower case to a full tower. I have always been a fan of smaller builds (mATX and mITX builds with watercooling are closest to my heart), so stepping it up to a full tower (the NZXT Phantom) was a pretty large step for me. But it wasn't really a performance increase.
Upgrading to my current 32" full-HD TV was also a large step as I had a 20" bulky old TV before. Image quality of movies went up tremendously, while normal broadcasting looked scaled and horrid. Still remember the first time I plugged in my 360 to it and was amazed at the picture clarity.
Hm, going back even further I reckon the biggest upgrade I have ever experienced was going from the old Mac I had to our first "home-PC" with a Pentium II and Windows 95. I used to play Unreal Tournament and GTA on that machine. And that was an upgrade from playing HUGO and a Flight Sim demo.