Jay (& Mike),
Delorme distinguishes between "Tracks" (actually walked) and "Routes" (planned hike).
Tracks: You can turn on "tracking" on the device and have your track saved to MapShare – as described by Mike.
Routes: You can create routes (and waypoints) in MapShare – manually or by upload – and then sync to your inReach. The limit of points in a route is 512. So if you upload for example Halfmile's GPX file for CA Section A, the 7160 twaypoints in it will be compressed to 512 points in the route. Since you mention that you are using your inReach together with a smart phone, I assume that you don't even need routes on the inReach. Just HalfMile's waypoints together with the Delorme Topomap on your smartphone should be sufficient. Otherwise you can of course manually cut the Halfmile tracks into shorter segments and then upload them to your inReach. I don't know what the maximum number of routes (or waypoints) is you can upload to the inReach.
Manfred

