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I'm migrating to Windows from Mac. I have applications on my Mac that require a license that itself is only for OS X. Before looking into running OS X via a virtual machine, will it be possible to use the applications installed on my Mac by simply copying them together with their dependencies (AppCleaner?) to the new machine?

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In short, no.
Windows cannot run Mac apps at all.

Also note that if you wish to keep to the terms of your licenses, that also includes macOS/OS X - which is only licensed for Apple hardware & not for virtualisation on other hardware.

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