Back in 2002/2003 in a former job, I ended up being the guy who had to babysit our VSS installation.
We gave VSS it's own dedicated server - real physical hardware - in order to minimize disruptions, and still we had regular problems.
Once a week I had to go and fix broken locks - locks that couldn't be released by the developer who placed them.
Around twice a year I had to recover from a corrupted repository - there seemed to be some kind of built-in limit at around the 1G mark, whenever the repository grew much past 1G things went bad pretty quickly.
Given that there are better tools - with better integrations - that are now available at zero-cost, switching from VSS (to me) is a no-brainer.