IIRC docker on Windows lives inside WSL, so everything is done on Linux anyway. What's the issues you're getting?
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Taking the time to learn the Linux command line, and how to configure a docker-compose file will pay dividends when it comes to docker.
Just remember to locally mount all volumes. Makes transferring to another host stupid easy.
I'm not sure what round arounds are, but can you describe the issues you have had?
I imagine you would install Ubuntu on your SSD, then mount the external drive in the Ubuntu OS, then install docker via apt.
Go Unraid. Great starting point for that kind of setup.
I would Recommend Using Hyper V for linux VM if you are going with Windows