Sync'ing from laptop to devices, via anything but iCloud, has gotten so much worse than it used to be. It used to be pretty good -- for it's time anyway. The ecology just isn't built for actual owned media anymore. And so many people have only a phone now, so no reason to try to sync. I think this is probably true on Android too. I don't know about the Watch, or what the documented ways are to get media files on it.…
Android in the past was surprisingly terrible at copying data to/from PCs. Anyone saying it works great is using some third-party tool that requires extra setup, or they aren't syncing a lot of stuff (media libraries, and iTunes used to also sync email accounts and some other settings). Aside from the lack of a proper syncing tool like iTunes, the basic Android File Transfer was super unreliable, often failing random…
Oh god! This bugs me so much. I don't understand why it's so hard to get this right. I'm sure it is, but why?
I know that if one of my devices switches from our 5GHz to our 2.4GHz network this can happen, but even when they're on the same network, it happens sometimes. (And why do my devices keep trying to force themselves off of the 5GHz network? WTF?)
And I get that it's called "Airdrop", but I'd really like it to work over ethernet, too, since that's a lot faster!