The iMac will be replaced with a custom-built PC.

The MacBook Pros are another story. I don't know. I can't see me buying any new Intel Macs since they'll be phased out at some point.

I've never had much luck with the Dell XPSes. I may give ThinkPads a look (I have a P50 at my current job which has been fine (if not for all the corporate antimalware slowing it to a crawl.))

Thanks for the response. I'm hesitant to move my family away from Macs because they have been relatively easy to support.

I'm hesitant as well, for the same reason. Having said that my personal PC (desktop) is still running well 3+ years after initially installing Windows on it. My inlaws' very old laptop is still running fine (it's at least 8 years old and was upgraded (on accident!) from whatever version of Windows it was running prior to 10.) Aside from user errors (accidentally installing adware toolbars in Chrome, etc) there really hasn't been any real issues as it pertains to Windows itself.