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One of the users in my team's site collection frequently experiences problems that I (the Site Collection Administrator) am invariably able to trace back to the user doing something in a very nonstandard way (e.g., downloading a document, editing it in the My Documents folder, then uploading it, rather than using the Check Out and Check In functions).

Would it be appropriate to ask a question about how to motivate this user to follow the more standard approaches to interacting with SharePoint (i.e., do it the way everyone else does it), thus preventing those problems from occurring?

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I don't see any reason why they wouldn't be. SharePoint, as you know, gives you a lot of ways to do the same thing, some being more optimal than other.

We talk a lot about best practices in varying degrees here, and user flow and behavior would certainly be no exception.

Having said that, the answers might get a little subjective, so we'd have to be mindful of that.

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