The TFS upgrade and migration has been a success. It certainly wasn't a smooth ride. It took me two rounds to knock the beast into place. The first round failed for some unknown reason, so I repeated the process but with a clean install of everything.
The upgraded TFS works fine except when you undo pending changes for source files. The undo process itself seems to be working fine, but for some reason it throws an error on the client side and logs an event on the server event logs. This issue is well described here (http://forums.microsoft.com/MSDN/ShowPost.aspx?PostID=2790907&SiteID=1).
If you like me upgraded the Sharepoint version on TFS2005 from 2.0 to 3.0, your sharepoint databases will most likely have a different name to that used by TFS2008/WSS3.0. During the database restoration proces, remember to restore to the database used by TFS2008/WSS3. Otherwise your Sharepoint Services will not work and you will not be able to add projects to your new TFS.
On my TFS2005 server, the WSS and the SQL Server Reports worked on different IIS port numbers. If you follow the upgrade process to the letter, you will end up with the same port number for both Reports and WSS. There are fixes for it in two different places affecting the Team Web Access, WSS Project Sites... Have to run along now. Will talk about this in another post.
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