VS2008 contains loads of bugfixes, and is definitely worth the upgrade IMO. Aside from improvements in the UI and related tools, it is much better at dealing with template classes, which didn't always work so well with the VS2005 compiler unless you were using the most basic syntaxes. There are also many other areas which have been improved, but I can't be bothered to find a MS document at the moment detailing these changes. So trust me when I say that there are many. :)
I'd say unless you have some compelling reason to stick with 2005 (ie, backwards compatibility of your code which doesn't build correctly with VS2008), you should definitely push for an upgrade. You can, fortunately, work with multiple versions of VS on a single workstation. You just need to install them sequentiall; ie, VS2005 first, and then VS2008 afterwards.
Then you could test your codebase under VS2008 and see how painful (if at all) a migration to VS2008 would be.