An aging Aunt and Uncle of mine ...
... found it faster and easier to use Netware, MS-DOS 3.3 with WordStar, dBase III+ and Lotus on an airgapped 25 year old network than it was to use the latest offerings from Redmond. I finally converted them over to a Slackware based solution[0][1] ... Their final year of using the legacy system brought them a tick over 1.5 million in sales, in 2015 US dollars. Not too bad for a small mom&pop family business!
[0] It was becoming quite spendy to get parts ...
[1] Yes, they required a little hand-holding at first, as would be expected, but now they have been using it for half a decade support calls are nonexistent. As in none at all for at least the last three years. Try to emulate THAT with your "more modern" Windows/Web/Cloud solution!