I detest Visual SourceSafe
Ranting ahead, obviously...
All our new projects are in bright, shiny Subversion repositories and humming along just fine. I've got about a month of detour through existing products in Visual SourceSafe and I'm already aggravated on the first day. Don't get me wrong, every source control system has some sort of problem, but VSS is the absolute worst.
The client is a piece of crap; it falls over and corrupts in a swift gale, it's slow, and hangs during CC.NET builds almost as often as not. Branching and merging with VSS is a joke. In a world where Subversion and CVS are free and reliable with multiple clients and integration into IDE's, and SourceGear Vault is inexpensive, why is VSS still so popular in .Net shops?
I've played quite a bit with the vss2svn perl script from Tigris.org. I have no idea if it works or not because VSS keeps crapping out on corrupted history trails. VSS won't even behave long enough to get rid of it.
One thing I'd really like to see from the .Net community as a whole is to stop taking everything from Microsoft without question. There is a whole world of development tools and knowledge out there that doesn't originate in Redmond.
How's this for scary though, in a former job we used VSS under the dark of night on the side because the officially mandated source control system (CC/Harvest ) was even worse.