You should encourage users to upgrade by not having history of things breaking -- it used to not be free, and now it's not free as in freedom with all the track

You should encourage users to upgrade by not having history of things breaking -- it used to not be free, and now it's not free as in freedom with all the tracking built in to the OS. I upgrade my Linux machine multiple times a day because I'm confident that things will be smooth and even when they're not it's usually one package at a time instead of the UI and all APIs changing on a monolithic release cycle. New versions fix up bugs and security, so we shouldn't be rolling with out-of-date software.