With Garmin watches you can drag and drop files over the USB connection. All of mine have worked fine until the battery life degraded enough to not be useful anymore (5-6 years).

Finding a good pair of wireless headphones to go with the watch is another story unfortunately.

RIP Zune, the best product Microsoft ever made. Mine died several years ago (the lock switch broke and it was a hassle to turn on/off) but I didn’t have the heart to e-scrap it until recently.