If the battleground for VSS vs. TFS will be fought anywhere it will be on this issue. As with any paradigm shift and change in the way things are done, it will be a challenge. Some will agree/like the change while others will despise it. A savvy champion for TFS in their orgnaization will recognize this issue and gain ammunition to sell it. Here are some great links:
Why doesn't Team Foundation get the latest version of a file on checkout?http://blogs.msdn.com/buckh/archive/2005/08/20/454140.aspx
Automatic retrieval of latest version on checkout?