Hi,
1. The simplify function in TF is very good at preserving detail and minimizing points. Have you tried it? Why do legs need to be 20-25 miles long, just curious?
2. Are you trying to upload as saved tracks or to the active log? If the former, the name is not important -- you get 20 x 500 points no matter what. If using the active log, you can have as many track segments as you want, with 10,000 points total, and the unit drops the name no matter what it is. Maybe you can explain more why it needs to be named a specific way? I have a lot of experience uploading tracks to that unit and I must be missing something.
Thanks.