@matigo So far, it's…going, albeit slowly.
@kdfrawg Getting her to upgrade is painful, so I only force the issue when necessary for security or functionality. We got a notice from Dropbox saying they were no longer going to support versions of OS X prior to 10.9, so it became necessary.
All the preliminaries finally being done, we are now upgrading my wife's 2011 MBAir from Mountain Lion to High Sierra. Keeping my fingers crossed.
I've seen corporate IT migrations that were less complicated than getting my wife to close all Chrome tabs and running applications in preparation for an OS upgrade.