I have been tasked with coming up with a strategy for branching, merging and releasing over the next 6 months.
The complication comes from the fact the we will be ru
My first recommendation would be to read Eric Sink's Source Control HOWTO - specifically the branches and branch merge chapters.
We have 3 containers - DEV, MAIN, and RELEASE for our work. MAIN contains all our "ready-to-release" code and we tend to think of it as "basically stable." DEV/Iteration (or DEV/Feature, or DEV/RiskyFeatureThatMightBreakSomeoneElse) are branches from MAIN and are merged up when the Iteration/Feature is ready to promote up past the DEV environment. We also have TFS builds set up from the DEV/Iteration branch and the MAIN branch.
Our RELEASE container contains numbered releases (similar to the "tags" container used in many Subversion repositories). We simply take a branch from MAIN each time - I like to say we're "cutting" a RELEASE branch to signify this shouldn't have a lot of activity going on once the merge is finished.
As for VSS->TFS - Microsoft supports an upgrade path which should keep your version history, but if you don't need it the history, I would just get the latest version from VSS, check it into TFS and archive the VSS repository.
One final tip - get your team members familiar with source control. They must understand branching and merging or you will be stuck doing a lot of cleanup work :).
Good luck!