This post is to highlight one of the important thing you have to take care when you upgrade your Source Control System from VSS to TFS,one of the major changes between both products is Checkout action is different than its behavior on VSS.
On VSS,Check out action get Silent Get latest action on the same action.
On TFS,Check out doesnt get latest of your files.
This feature is not available on V1 of TFS & VS 2005 and this will be availble on Orcas.
As a Temporarily solution,you can download an add-In to do that for you,Get Latest while checkout your files in TFS........
AddIn Download Link :
Hope this helps.