Hi,
Seems like a pretty good strategy to me. There isn't a way to display the name of a file in the map in TF, unfortunately. You could certainly add such text as waypoints, but that might be tedious if you have a number of files loaded?
A toggle that shows the names (and numbers, when there are multiple tracks per file) is a pretty good idea. I can't guarantee it wouldn't get cluttered in some cases, but it would help for your projects and also in identifying tracks.
Thanks for the post.