If you feel so upright on a Dolce, are you sure you need a WSD bike? Have you tried the Tarmac or Roubaix? Cannondale CAAD9? (Great bang for buck--don't let the lack of carbon fiber here make you think it's not as good as carbon unless you're interested in being an upper level racer). With something like the CAAD9, you can put more of your budget into quality components. Of course, I love my Specialized. I recently did a drastic frame upgrade, and it is sooo much better. A lot of that is weight, though. Still, I think a enormous upgrade in frame is a tiny bit better than the jump from, say, 105 components to DuraAce. However, if you want it to be your last bike, don't skimp on components either. 105 is pretty durable. Ultegra gives you durability with better performance (better braking on hills, smoother shifting). So, with Specialized, you'd be looking at a $2k+ bike, unless you find one on sale, if you're going with carbon.

The Dolce is very entry level, and it's a fine bike for sure. It's heavier on those hills, and it's not going to make the group rides as easy as the carbon bikes, if for no other reason the geometry differences.

If you're really getting into road biking and want to spend a LOT of time on the bike, then you will likely be bitten by the upgrade bug at some point. So, again, get the best quality frame and components you can afford now, and then you won't be making that many changes down the road, as tempting as they might be.

Another thing to consider with your budget about Cannondales is that they have a great crash replacement policy. I believe $400 gets you a new frame. Period. Specialized will offer you a discount on a frame or new bike, but it's going to be a lot more than $400. A crappy thing about Cannondale is that they use proprietary cranksets, so if you trash the bike but have useable components, you're going to be buying another Cannondale so that you don't have to shell out a couple hundred bucks on a new crankset. BTW, Cannondale also has WSD bikes if you think that geometry is really what you need. Don't assume it is, though.

Pretty soon the 08s are going to be on sale, so keep that in mind. If your shop has any 07s hanging around, you might want to look at those for some good deals, but sizing will probably be limited.