I've almost never seen an iMac require attention after setup. When's the last time a PC tower operated by nontechnical people ran nicely without IT attention for 5+ years?
In this case, OP mentioned Erik's did have an "IT" employee. I'm guessing the IT individual's knowledge did not extend to having dedicated POS machines or understanding the concept of user profiles and group policy/rights. With cloud-based/hosted POS systems now, security concerns don't necessarily stop at one's browsing/computing platform.
The $6 usb/wifi dongle from Monoprice stays connected for weeks at a time.
As long as we're pulling out anecdotes, I've put together PC's with that service lifetime, for use in business. I've serviced brand new iMacs that don't support certain printers, or other hardware, and the users of these require very much attention indeed.
Why would their software suddenly stop working on old hardware?
Try to find a modern version of some software on OSX 10.4, for example. Development has likely frozen years ago, meaning bugs won't get fixed, security is out the window, and everything sucks forever.