Visual Sourcesafe vs SVN, AnkhSVN, TortoiseSVN
I have worked with used Microsoft Visual Sourcesafe and now in my current company, we are using the SVN-Tortoise-Ankh combo. One thing i noticed though is that teammates really have to communicate. Although we are just two in the team, in order to prevent the tedious conflict resolutions, we needed to tell the other which part are we revising/coding.
Unlike in VSS, a user checking out a file is warned when others have it checked out (FYI: VSS has allow multiple checkouts configuration which is off by default), so if one's changes is not a priority, he can wait for the other user to finish his changes before applying his own. I couldn't find this feature on our current setup which i think is a very useful notification.
[EDIT] As i've said, if you have multiple checkouts allowed, you can ignore the warning and proceed with your changes. The last man to check in will do the conflict resolution (although i admit, vss conflict resolver sucks).