[snip]
>Do you allow Multiple Checkouts? If not, that could be screwing up the projects. I have gotten this to work before....

First of all, nice to *see* you again! I'm finally off the MS newsgroups, since we decided to switch over to the UT in our shop. Hope you've been doing well!

The way I understood the problem was that after the 2 developers' projects were set up under VSS, one of them added a file to the project and source control.
The other then did not get the updated file.
The only thing we have found that works to *automatically* get new files is to re-join the source control project. We don't really want to do that, so we have to manually copy the file(s) over to the development machine, add them to the project, add them to source control, get the source controlled version (when it tells you that it's already under source control).

We also haven't got pinning or rolling back to work with VSS, either.
Have you ever got these to work?