I've just finished upgrading my site to Community Server 2.0. Well, my opinions are mixed at this point at least from an "administrator" point of view. Although the interface is more complex and with a lot of new features I was kind of puzzled that out of the box the configuration file is kind of damaged. The fix is straightforward, but still... for a piece of software that wants to be RTM is quite annoying. (For more details you can drilldown on Community Server forum: ). And, yes, others were puzzled by this quality of this release, too.
Anyway, I overcomed all the issues and the upgrade was very smooth. Basically, the longest operation was uploading of the new files, and they are quite a lot. Applying the upgrade script worked flawless. In the same step I've switched to ASP.NET 2.0 so I'm pretty much up to date right now.
As a side note, just after updating the installations I've seen on the Community Server site that they are planning for 2.1 release to be available in July 2006. So I should start planning for the new update.
One of the reason of upgrading to 2.0 version is that I found a very nice tool named CS Gallery Manager that can be used to upload multiple pictures in one step. Although it supports CS 1.1 with a small hack, I thought it's better to upgrade. The great thing of CS Gallery Manager is that it supports both rotate and resize on the fly, so you can keep it on the desktop or laptop machine, plug in the SD card of your camera and you are good to go (actually your pictures :) ).