Why Why WHY doesn't TFS's get latest work consistently?
You would have thought that feature would have been tested thoroughly.
What I have to do is, get specific version, then check both overwrite writetable files + overwrite all files.
Is my local setup messed up or you do this also?
TFS redefined what "Get Latest" does. In TFS terms, Get Latest means get the latest version of the files, but ignore the ones that the server thinks is already in your workspace. Which to me and just about everyone else on the planet is wrong.
See this link: http://blogs.microsoft.co.il/blogs/srlteam/archive/2009/04/13/how-get-latest-version-really-works.aspx
The only way to get it to do what you want is to Get Specific Version, then check both of the "Overwrite ..." boxes.