My father was willing to switch, my mother was not.
So: my father is now on his third Linux machine in 16 years (two laptops and now a NUC hiding behind a 24" monitor). Normal updates are handled automatically; I do a major upgrade once a year. rsnapshot backs up to an external disk three times a day. Every so often he tells me that he wants to do something new, and asks if it's possible; the answer is always yes.
My mother is on her fifth computer in that time. She's always unhappy with it, but refuses to change, because she's afraid that Linux will be incompatible with the new service-du-jour that her friends are always adopting.