I found this tool called too long path detector. https://sourceforge.net/projects/tlpd/ It will dump things to a text file so you can show your users how lame they are. Source: about 2 years ago

I, unfortunately, was lead on a project to move file server data to SharePoint for several departments. While your post may be in jest...it was the bane of my existence for a time. This tool (TLPD) was a life saver, I sent the reports to the specific departments for users to reduce the length. Of course there were many who ignored the repeated request, so I wrote a PS script to cut down on spaces and change... Source: about 3 years ago

This app is invaluable for these types of questions https://mactracker.ca. Source: about 1 year ago

I use a tool called Mactracker. They update frequently to keep up with obsolete/vintage status and have a macOS app and iOS app. If you click the Software tab in the app you'll get Maximum OS. Https://mactracker.ca/. Source: about 1 year ago

You can also use the mac app Mactracker -> https://mactracker.ca/. Source: over 1 year ago

I remember running into a FileMaker database file which contained a list of all Mac hardware, including playable embedded AIFF files of what their startup chimes sounded like. I feel like a librarian in the Library of Babel talking about the pre-prehistoric Internet. Then again, maybe it was an old version the MacTracker app: https://mactracker.ca. - Source: Hacker News / over 1 year ago

Which is all interesting as the screen they are showing I think is high Sierra which supposedly the early 2009 couldn’t run only the late 2009. As per the mactracker app. Source: over 1 year ago