Have you upgraded from your first road bike?

[tinycities]

i just bought my third bike.

i started off with a hybrid about 4 years ago, then bought a terry geometry bianchi that i just sold to a fellow TE member.

what caused me to sell that was learning way more about bikes than i knew before, and knowing the bike fit me wrong. the person who bought it seemed way more at home on it than i ever did!

but knowing what i wanted [ horizontal dropouts, tire clearance but with road bike geo ] i got fast measured and was fitted to a salsa casseroll which fit me perfectly. now i'm building that up how i want it and its awesome knowing all this stuff about bikes and being able to put exactly what i want on it.

[Crankin]

I started riding in fall 2000, on a hard tail mountain bike. After 2 years, I bought a Cannondale R600 for my first road bike. I guess it fit OK, but the aluminum was jarring and the components were cheap. I constantly was dropping the chain and unable to shift. Exactly a year later, I bought a Trek 5200, 47 cm wsd. I had that bike from July 2004 until July 2006, when I got my Kuota. After fighting with the lbs for 2 years, they exchanged the frame for a smaller one, different model. But, I don't really count that as new, since I didn't pay for it and they were the ones who pushed me into buying the first one. I finally have the right brifters, bars, etc. I like my bike, but I have never been entirely pain free on a road bike. In retrospect, I maybe should have kept the Trek, and tweaked a few things.
I am thinking a good present for myself when I finish my grad program might be a custom bike, a tad more upright, but still a road bike. It probably won't cost more than I paid for the bike I have, though. I have never really had "bike lust" for a particular bike, so I might let the feeling pass and just keep riding my Kuota until I really need something different.
I bought a Jamis Coda for errands and around town riding in 2008. It fits right and makes me happy, although it feels incredibly heavy to me.