We are updating a fairly large solution (20+ projects) from 2005 to 2008, but it was really trivial. Updating a project is only basically. The underlying structure is still the same, since 3.0 / 3.5 and 2.0 use the same basic structure.
As mentioned above, despite the fact that you are updating, you do not need to change the link to the infrastructure for projects - in fact, by default it leaves the structure in 2.0 instead of changing it to 3.0 / 3.5. This means that you will not be able to use the 3.0 / 3.5 functions until you change the link (Project Properties Page, Application Table), but it also means that you are much more confident that there will be no additional support (how do you get the error with the addition of code 3.0 / 3.5 until this link is changed).
The new features of TFS 2008 should not be overlooked, although you do not need to update the application to be able to use TFS 2008.
From 1.1 to 2.0, the conversion was much more painful ...
ScottCher
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