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When I was still dual-booting Windows and Linux, I found that “raw disk” mode virtual machines worked wonders. I used VirtualBox, so you’d want a guide somewhat like this: https://superuser.com/questions/495025/use-physical-harddisk-in-virtual-box - other VM solutions are available, which don’t require you to accept an agreement with Oracle.
Essentially, rather than setting aside a file on disk as your VM’s disk, you can set aside a whole existing disk. That can be a disk that already has Windows installed on it, it doesn’t erase what you have. Then you can start Windows in a VM and let it do its updates - since it can’t see the bootloader from within the VM, it can’t fuck it up. You can run any software that doesn’t have particularly high graphics requirement, too.
I was also able to just “restart in Windows” if I wanted full performance for a game or something like that, but since Linux has gotten very good indeed at running games, that became less and less necessary until one day I just erased my Windows partition to recover the space.
We’ve found it to be the “least bad option” for DnD. Have a Discord window open for everyone to video chat in, have a browser window open with Owlbear Rodeo or Foundry / Forge for your tokens and character sheets, all works smoothly enough. The text chat is sufficient for sending the DM a private message; for group chat to share art of the things you’ve just run into or organise the next session.
Completely agree that for anything “less transient”, then the UX is beyond awful and trying to find anything historical is a massive PITA.