The TFS team over at Sela , spearheaded by Tal Gur Arie,  had developed a little addin that solves the issue with not getting the latest version of a source file when checking it out. They have their reasons for doing it, and there are a couple other Addins that do this, but this is the only one i know that asks the user if they actually want this to happen:

"How does it work? When a user checks out files, the Add-in checks if the file version is the latest, if not - a popup message notifies the user that the current file is out of date and if enquires whether he/she would like to perform a "get last version" action. If the user selects Yes the Add-in will perform get last version automatically. "

More information here