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Hi Soren,
Yes, XOOPS is awesome indeed, I tried about 10 other CMS style management systems, and XOOPS was by far the easiest to use and set up.
There is a hack that will allow your users to log in automatically when they visit, and it also allows you to set the duration they will be able to autologin. You can get it
here.Im not sure how to code it, but there are a few themes that display Welcome "Username", I know for sure that 7dana-jane theme has it. You can download this theme from their website:
7dana.
There is no telling what will be overwritten when you upgrade to new versions of xoops. Most of the more popular mod authors keep thier work up to date with the newest XOOPS code. Im quite sure that the CVS files are always available prior to updates, so you will always have good notice of at least the types of changes that will be taking place, and plan accordingly. (of course there is always a chance that any changes won't make it into the final release)