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Windows Docker is so bad, I don't even know why it's a thing.
Some good planning might make the migration less painful. I would recommend a ZFS or other COW storage solution under the docker host so you can do snapshot backups and not have to worry about quiesing databases, etc.
Yea I'm gonna do zfs or something when I get set up properly again. I've got 2 16TB HDDs and Storage Spaces won't let me pull a drive out :v
I think I'm gonna have to make a new Storage Space and slowly grow that one and shrink the other as I basically shift the extra storage budget between the two until the data is on just one of my drives without redundancy, and then I'll pull that drive, dual boot Ubuntu or something, format, get everything prepared, and then mount, copy, start services, and then go back and kill the old storage spaces and then never run Windows for anything meaningful again.
Check the returns policy, but if you could buy a large external drive at something like BestBuy, do your copy then return it, that might be a lot safer than what you're talking about. Just a thought.