What I do is check to make sure I have the most up-to-date version every time I use an extension that I haven't used in awhile. Then I check the forum for stickies on Known Issues.
The new layout for the Downloads page makes it very easy to check all versions by opening up Extension Manger next to the list of extensions. If I find that one of mine is out-of-date, I delete it from Extension Manager and download the new version. This prevents me from accidentally trying to install a new version over the old one and corrupting my cache.
After I have all the new versions downloaded and the old ones removed, I start installing them one at a time deleting the cache after installing. This method has allowed me to avoid the common problems with DW.