Over the years I have went from using no source control whatsoever (from around 2000 to 2004-2005) – mostly because, I was a lone developer, and also you really don’t learn about it in college, and I just never looked into it. Another reason is that there weren’t many good source control apps for Windows NT/98/2000, or at least I didn’t know about them. CVS or VSS.
CVS is ok, but clunky. SVN the supposed replacement to CVS is pretty awesome, works well, and is easy to use. On the other hand, VSS, VSS 2005, and then TFS source control paths are different. VSS 2005 is OK, but still has issues with locking, you can tell they don’t use it at Microsoft. The version before that is even worse. File open dialogs from Windows 3.1 era. Just a mess.
I have seen places use VSS in a way where they would be better off just taking a zip file snapshot every hour and copying it off. Instead you have crazy directory structures and a hard to use “tool” that causes you more headaches than anything. Hard to see the status of the files in Windows Explorer, etc.
About a year ago I wrote about using source control at home, SVN to be specific.
I guess just from my experience steer clear of VSS if you can, and use SVN, get TortoiseSVN and/or VisualSVN or whatever you need, even CMD Line, just please don’t use VSS, it just makes life harder than it needs to be.