I'll add that team builds in TFS will greatly reduce the amount of time you're spending doing production builds, and it will be trackable, controllable and repeatable.
Also, TFS provides an import utility so you can import your VSS source, including the history to TFS.
To answer your specific questions:
1) Team builds on one or more dedicated build machines will fix the pain involved in builds and will very likely make them faster. Getting source in TFS is much faster and more efficient than it was in VSS.
2) The SQL backend of TFS prevents things from getting "messed up." There's a few things that work differently in TFS that may cause your users to think TFS didn't do something right, but every case I've ever seen is actually the user misunderstanding how TFS works and is quickly correctable.
3) Sharing files between solutions can be done, but to do it properly means that the shared code should be in a shared *library*, not in a file(s) that are referenced by multiple projects. This has nothing to do with TFS, but is fundamental to successfully reusing code.
If shared libraries are not possible, then the problems of sharing files could potentially be mitigated with something called continuous integration - that is, anytime a file is checked in, the appropriate builds are fired off automatically and any builds that break due to the checkin will be known quickly. This works well when the actual compilation of a project is on the order of minutes, but not so well when it is on the order of hours.
MS does not recommend VSS anymore for the same reason they don't recommend MS Access - database handling done with only a client via a file-share is prone to corruption.
TFS is not simply an upgraded version of VSS - it was an entirely new product written from the ground up. Even if TFS is only used for source control, it is still way better at that than VSS is.
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by: ripahoratiuPosted on 2009-09-08 at 00:39:19ID: 25279405
Well, Source Safe is simply a Source Management Tool TFS is much more than that. Except the fact that TFS as source management is using the SQL engine to manage the sources, and has better source management capabilities, is much more stable and can be used in large environments (meaning large teams, believe me, you don't want to see what's happening when you use VSS with 50 users working on the same solution), works better in concurrence and has a better conflict resolving management. That's for Source Management only, and, indeed, MS highly recommends it against VSS.
But furthermore, TFS is a great tool for the entire management of development, that offers you the possibility to create/associate the documents, iterations, assign tasks, bugs, issues, roles, versions, and so on and keep the whole thing together, in a single organized place. It's also a bug tracking tool, a project technical management tool, and if it is properly used one can have a very good image on project progress and status. It might have a painful learning curve but my opinion on it is that it is a great tool, once that everyone begins to use it properly. It is not a silver bullet, and have sometimes problems but not major problems - it will probably reach maturity these days - but is one of the best management tool on the market, and for MS VS solutions is surely the best since is integrated with VS.