Upgraded from my cheap, slow, heavy
Diamondback Kalamar hybrid to a much lighter, much faster, much more expensive
Kona Dr. Dew urban bike.
The Kalamar was never intended for long-term use. I bought it as an experiment, figuring that if I really took to riding I'd replace it in about a year. If I didn't take to riding, it would get mothballed and I wouldn't be out too much money.
I went with the Dr. Dew because I needed a multipurpose ride that would be an effective all-weather, all-season commuter under about $1200 (and preferably under $1000). That meant disc brakes were a must. I originally wanted a Dr. Fine for the Alfine IGH, but they were out of stock, period, so I settled for the Dr. Dew. Compared to other possible commuters I looked at, I liked the riding position of the Dew line better. As a bonus, the hydraulic disc brakes are pretty sexy. I love the power and control they give.