It seems the hardest part of being a Team Foundation Server admin is the 'This is how things worked in Visual SourceSafe' way of thinking.
Well, today I came across a legitimate gripe.. the status icons of a file do not always update properly, even when you do a 'get latest'.
I found a way around it, but frankly this should be default behavior:
http://devmatter.blogspot.com/2007/07/refreshing-tfs-version-control-status.html