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Moved my father-in-law from Windows 10 to Mint.
Biggest problem was all his 'documents', which were office365 web links rather than 'actual documents'. Linux presents them as the urls that they really are. They open just fine, though, and can be exported as real local docs for libreoffice etc.
Security and privacy were the main selling points for him. He'd done some reading and thought that Mint was among the best choices for a newstart that just want everything to work; no interests in playing games or anything. I agreed that was the most solid choice. I use Arch btw myself, but wouldn't recommend that for beginners.