Unable to sync Waypoints or Tracks from Map to GPS

I have some custom waypoints and tracks I want stored on my device for an upcoming trip.   I imported the tracks from an older GPS to the map share site, created a new collection and setup the waypoints I wanted.  

This collection is marked to sync to the device, but when I sync via the (totally horrible) phone app or via cable, none of the waypoints or tracks will sync to my device. 

It's getting really frustrating and I am tempted to switch back to my old trusty 60csx as this always worked and I could get what I needed for this trip as I really need the waypoints / tracks. 

Things checked:

Under Devices --> Sync --> Collections | Collection in question is checked to sync.

Under Map --> Collections | All the data I want is part of said collection.

Under Map -- Collections | Sync to device is checked. 

On In-Reach:

Waypoints --> Empty

Map --> No tracks, no waypoints.

On App:

Waypoints listed, but when clicked, nothing on map.

Tracking shows no tracks, (Tracking button crashes the app ~50% of the time)

I've had really poor luck using the app to do anything with the GPS, the stability/quality of the app is extremely poor.  I do 90% of my syncing via a hard line to make sure my data is actually pushed to the cloud. 

How do I get this data on my device and be able to view it?