I noticed that firmware 9.50 has a change for device transfers, so I tried a transfer of a course between my two Edge 1030 units.
The units are sitting side by side on my desk. I powered on the older one, then the newer one, and went into the settings, selected Connected Features, then Device Transfers. Both units are showing the spinning circle (looking for nearby connections. After waiting for a minute or so, I picked up the older unit, selected Share Files, Courses, and selected a course that isn't on the newer unit, and pushed the check mark at the bottom right of the screen. After a couple of minutes, the newer unit showed "(BT)Edge 1030" with an arrow on the right. I pressed the arrow, and the course name showed up, with a check box. I pressed the box, and got a check mark. Then, I see a screen that says "Transferring 1 File", and has a spinning wheel with a zero inside (presumably the progress indicator). After a couple of minutes, I got a message at the bottom of the screen: "Transfer Failed. Try again"
When I look at the newer unit's courses, the course I just tried to transfer appears!
So, in summary, the two units never seemed to find each other, yet I was allowed to select a file to transfer, and start to transfer it. The transfer failed, yet I find the file has appeared on the newer unit. Backing out to the start screen, I can press the Navigation button, and find the course on both units.
This is terrifically helpful!