I see it a bit as a REST thing: /v2/some/endpoint implies that v2 "owns" "some/endpoint". What state does "v2" represent? Does it own every "some", just "some/endpoint"? What is that hierarchical relationship really?
It's a general problem I see with any REST API that tries to version that way. Version isn't a strict hierarchical "owns" relationship and embedding it early in the URL sort of violates REST principles in what the folder path of a URL is meant to imply. (Admittedly, that's a bit of a more strict interpretation than most people pragmatically follow when building REST APIs, but it is an interesting and useful strict interpretation so worth bringing up and examining.)
If you are versioning individual endpoints it might make sense to use URLs like: some/endpoint/v1 and some/endpoint/v2
That makes it more clear that "some/endpoint" "owns" that relationship and kind of/sort of what "exactly" is being versioned. If you must put a version number in the URL.
That said, REST has always been about content negotiation as a long held tenet, and that has always been about using the right Headers (since the earliest HTTP 1.x apps), and I've always felt like complaints that you can't send the right version Header reflects primarily on bad tools that don't understand HTTP (and REST) as well as they should. Sending Headers is an important part of HTTP. I don't think it should be harder to send the right Headers than to embed things that would be Headers into the URL. Though that's just my somewhat strong opinion on the subject.