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@salad
Definitely try with the Anker hub - sometimes dongles etc. don't like them, but it will probably work fine.
Regarding learning the new OS - actually, I haven't heard of a lot of people having a hard time.
Sure, some things are different, but mostly stuff just works and they're happy.
I transitioned two people in their late sixties who used Windows all their life to macOS and they're both super happy they have a mac now and do not bitch at all 💁