Just to make it clear to any other people reading this, Jellyfin has Group Sync where you can create groups with participants and syncplay media.
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over to Linux full-time back in ~3.15. I recommend you join the LUG Org (Linux User Group), as they have a load of resources in case you get stuck and have some people working on specialised Wine runners. They also run a Matrix Space that's worth joining.
For email and VPN, I recommend Proton. Even their free tier works well.