Since I had some trouble doing this the other day I figure I would post the solution here for future reference. For some reason if you check in a symbolic link to a directory and then later you want to replace that symbolic link with another type of file (say a directory or regular file) you may come across a problem where Subversion thinks you want to delete the directory that the symlink is pointing to. Here is what you need to do:
svn del --keep-local symlink
svn commit -m "removing symlink"
rm symlink
svn up
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