VSS has two "modes" of checkout. One locks the files, the other merges on checkin. Locking is the easiest way to prevent breaks, but can cause a loss in productivity as others have to wait for the check-in to work on the code.
I'm not really certain what you mean by "breaks" here though. Do you mean merge conflicts?
Do you mean link breaking? Do you mean that people can get code that is broken?
If you mean people are getting code that is broken, VSS doesn't have a transactioned and atomic commit system, so there are times when a pull can pull files in mid-change, but honestly i've only run into this a few times.
I wouldn't use VSS for a distributed development environment. It's ok to use it for some off-site development where your primary work is done on-site, but if your primary work is distributed, i'd choose something more client-server oriented with transactional commits and change sets.
UPDATE: Yes, VSS has automatic merging, however if two people edit the same file, and those changes overlap, it takes human intervention to merge those changes. VSS will pup up a window that allows you to choose what to merge. This is the same for any product.
BTW, ClearCase is RIDICULOUSLY expensive.. $100k+ in many instances.
Also, VSS does branching quite a bit different from ClearCase or many other products and has no promotion model like what you are referring to. You have to check in the file, then merge the branches to get them into an earlier part of the branch.
It sounds to me like you want to use version control in a way that VSS is not the best fit for. I wouldn't recommend Subversion either (as many like to. It's a great tool, but it's not as user friendly as VSS), because it does have some learning curve and it's GUI tools are not quite as intuitive as other prodcuts.
You might consider SourceGear Vault. It's a good product, easy to use, and provides the robustness and features you're likely looking for at a reasonable price. They also have an evaluation version and can import SourceSafe databases.