I know what you mean about being spoiled. I just got my first single. The first "real" one anyways. I had a basic cruiser for a little while for riding around with the kids, but the first time I tried to go on any sort of real ride to get real exercise .... was pretty much the last time. That was a couple of years ago.

DH and I got a tandem road bike last year and eventually I decided I was ready for my own real road bike. I feel completely spoiled with my beautiful Cannondale CAAD 9 with Dura Ace components, weighing in at 16.60. I LOVE IT!!! Part of me thinks I don't even know how great I have it since I've never had to struggle with anything else, but then again, there was that cruiser! And the 10 speed I had in high school in the 80's! So, maybe I DID pay my dues!

In regards to your question about your winter bike, I agree with Starfish in that you should spend as much as your budget allows. You know how wonderful it is to ride a really nice bike and you'll be more likely to get on it and enjoy it if you get the nicest one you can reasonably afford. The problem is, nobody can tell you what you can reasonably afford. I have no idea how big of a deal that extra $400 is to you right now. I don't want to tell you to spend that extra money and then find yourself without electricity because you couldn't afford your bill!

Well, I hope that was somehow helpful.