In my current job, I can point out something that might be a contributing factor: I work in an industry where there is basically one 800lb gorilla of a vendor.

In my current job, I can point out something that might be a contributing factor: I work in an industry where there is basically one 800lb gorilla of a vendor. They update rarely, because their product is a mission-critical, life-or-death sort of thing. Their current product is heavily, heavily integrated with x.y.z version of software from a different vendor in a different segment, but also weighing in at 800lb. Yes, they specify x.y.z, not just x or even x.y. That software comes bundled with a Python 2.7.5 distribution. Imagine my woes trying to get pip running, which unhelpfully suggests I upgrade Python. Cannot seem to find any other path to even get pip going because of what I call the "lol just upgrade n00b" factor. Perhaps that information once existed but I cannot find it. So, I am stuck on this version because of some pretty tight integration, at a couple of removes. I think the vendor-linkage can cause some "drag" that folks who work in a greenfield environment might not be thinking about. It can be unfortunate but there it is.