>shed some preconceived notions
Not to mention that on Windows, it seems you have to shed preconceived notions of how to configure it from version to version.
As an example, why did they ever change the control panel's "Add/Remove Programs" to " Programs and Features"? Or whatever the heck they renamed it. Or the Charms-only approach to Win 8.x wifi configuration that is such a change from XP/7.
I am sure Linux grumblers will point out that various distributions change their configuration apps a fair bit. But a power user can usually fall back to command line configuration or at least use the command line to report system status. And, well, for better or worse, people who configure Linux are expected to be more flexible.
OSX's System Preferences are also quite stable from release to release - that's something MS could learn from because the majority of its user base is the equivalent of Windows consumer-side users.
Worth the effort? Depends on your needs, skills and expectations. But I will say that a Linux box, once configured, tends to be a lot easier to keep updated than Windows. Applications are generally transparently and centrally updated. You don't get a zillion startup programs all independently querying their respective vendors to see if a patch is available. Nor do you get the maybe/maybe not Windows patch reboot sing and dance. The home directory is not a confusing mix of user data + application stuff - you can copy it from machine to machine and be assured that things will work.
The OS is a lot better, I think it mostly depends on whether you have the programs you want to use on Linux. And a VM can help there as well.