To those of you who have worked with WordPress for a while, how soon do you typically wait before updating your sites to the newest version, once it's released?
Since most of the updates are to patch known security holes - as soon as I find out that there is a new version. After all don't want someone to use the newly patched hole to trash the site before the patch is installed.
My concern is that the plugins may not be compatible. Do you find that to be an issue?
For most of the minor security upgrades there shouldn't be an issue with plugin compatibility unless the plugin is a security issue itself. You may want to check things out a bit more before installing a more major upgrade but those are relatively rare.