I've been somewhat reluctant to upgrade my DSLR, since I don't use it very much. For most of my excursions a DSLR is too cumbersome and heavy, since I prefer to move with lighter gear. The compact camera Canon S90, which I bought this summer, is one of the absolute best compact cameras when it comes to image quality and it is truly pocketable. I've been very satisfied with it. However, a DSLR gives better image quality, especially when it comes to dynamic range and high ISO images. The sharpness is also better, though this depends heavily on the quality of the lens. I've been photographing with Canon EOS cameras since 1990, and have some nice lenses. I bought the 6 MP EOS 300D, the first consumer priced DSLR, when it came in 2003. While its image quality still is better than the best compact cameras of today, it is somewhat slow. To replace it I bought a second hand EOS 40D. With its 10 MP it has a lot less pixels than the newest ones, but the pixels should be very good. It also has a lot more direct controls than the 300D and a very nice viewfinder. If I had more money to use, the natural choice would of course have been a 60D, but for most practical purposes, the difference in image quality is marginal, though the 60D has some ergonimical advantages, most notably the tiltable back display.
I also contemplated the Sony NEX series as an alternative. The concept is great, but the lens selection very limited and to replace my current lenses would be very expensive and they are not even available yet for the Sony NEX. The mirrorless design does seem nice, but in practice the cameras are still not small enough to be truly pocketable.
It remains to be seen how much I will use the camera when riding my bike. I would probably need a minimal backpack for it. The Lowepro Slingshot 100 AW seems nice: small enough and quick access to the camera.
Below are a few test shots. The first one would really need a HDR technique for optimal result, but this photo still shows the difference against the S90: There are lots of details in the highlights (sky), while the foreground is still not too dark and noisy. This would not be possible with a compact camera (except for HDR imaging).
The Pugsley got a front rack, and hence should be ready for the beer ride next weekend.