I've been tinkering with the idea of writing a service agent that detects when my Garmin GPS watch is connected to my desktop (where / how I charge it) and automatically pulls down any new activities to store locally as a backup.

Starting around 2012... I used to scrape my activities off of the Garmin Connect website, I eventually got tired of the manual nature of this process and also having to keep up with changes they made to their site. After that, I used something called, I believe, Tapatirik, for a while, to automatically sync them to a Dropbox account. But, it wasn't flaky sometimes, so I eventually gave up entirely and just turned on the sync to Strava option. But that also has spurious failures that are annoying to deal with. And on and on it goes...

Frustrating is one word for it. I'm at a point where I find it to be completely anti-consumer.