Hey Derrick,
Where are you naming the track? In File properties, or track properties? (there is a difference, since each GPX file can have a name, as well as each track).
Figures, I just mailed my Dakota out to Matthew for Trans North Georgia so I can't test!
When I uploaded the Georgia track for him, though, it came up as TNGA.gpx -- the name of the file. Maybe the trick is to not name it anywhere in TF?
Oh, I don't think I was using "Where to..." either, just looking at it in Track Manager and turning it on in the map. Also, you may try using TF to upload instead of copy/paste. I think there's some code that makes sure it has a good name. That might be the issue there.
Try it and let me know.
