GC will definitely be moving up to vBulletin version 3. It has a number of new and improved features. I've been planning for this to happen in the spring of this year - so sometime within the next few months. GC is currently using the most recent version of vB2 which was released in January.
Prior to upgrading to vB3 I'm also planning to upgrade the webserver to a new and more powerful one. A bunch of testing & other details will need to be taken care of first with the server upgrade before getting along with the vB3 upgrade.
One other issue that may possibly hold us back on the vB3 upgrade is a bug in the PHP 4.3.10. I'd like to have the most current & stable version of PHP when GC vB3 goes on the new server. The bug in PHP 4.3.10 causes high server loads & generally slows things down a lot, you can see the details on that at
http://bugs.php.net/bug.php?id=31332 PHP 4.3.11-dev has a fix for the bug, but I'd rather not upgrade to that until it is released as a stable version. If PHP 4.3.11 is not available by the time GC's upgrade to vB3 is on the way, I might just use 4.3.9, but will see when that time comes.
I'm not sure yet about which optional vB3 features will be enabled on GC. I'll be looking into all of that in the coming weeks. Regarding avatars & attachments: not sure at this point due to bandwidth & database size considerations.