I have went thru my working version of my project and removed a number of extraneous image files that are no longer being used. When I do a check-in will these images also be removed from TFS or do i need to remove them in TFS as well?
I'm guessing they won't be removed from TFS, the whole point of content management is to provide a step back to how things were if mistakes get made, so I would expect the images to remain.
Conduct a test, remove just one image (keep a backup) and see what happens. If you are happy with the result you can press on, deleting the backup if necessary.
Steve Life's too short for bad coffee, bad chocolate, and bad red wine.