1) locks on documents that have been checked in
2) server too busy messages
3) cumbersome hierarchy (that's particular to how this was set up in 2008)
4) saving a file has to (in order) save version locally, upload a history, upload version, upload workflow... and you don't get error messages from the uploading tool if your workflow doesn't save, meaning you can't access the version that was uploaded
5) (company specific) only one person in the organization can adequately care for the system and he's a consultant who has a backlog for 8 months