I have customers, preparing payroll for others, that are griping because they still want to use XP or another obsoleted OS (By the maker of the OS). At the turn of the century, I had some who did the same, insisting they could only use a DOS based OS. I have some who are in "business" claiming they have no internet access, which I know is untrue (except for a monastery), and they must have a CD. (Wayfair makes it untenable to continue to offer CD's based on how certain states implemented Wayfair, and the minuscule number who still ask for a CD.)
If I were to have someone else handle data for me, I would ask for information showing their hardware and software maintenance policies and status.