>I am aware of how VSS works, but as I am anticipating a similar situation arising where I may have multiple versions live at the same time, I am wondering how VSS can help me maintain these separate versions.

You may have multiple projects in VSS that map to the same directories, or partially map to same directories but some of subdirectories point to different actual locations. You can get quite creative with that, to the point when you don't know what you're doing :).

This means you may have (physically) multiple copies of the same directories on the server, which actually map to different directories on the client's machines, or vice versa. It can get quite confusing if not exactly everybody is on the same page with the scheme you create. And it's possibly confused in my head, becase it was about three years ago now that I last used VSS.