Re: a slow motion trainwreck
Not directly related, but did anyone notice that Win10 doesn't support the old .chm help file format? Really great when you have old software that still runs, but w.o. help files.
The writing has been on the wall for .chm help for a LONG time. The WinHelp viewer (the program that displays .chm files) has not been included with Windows since Windows XP (Vista was the first version not to include it).
The WinHelp format was deprecated because it is possible to write malware that exploits the format, so that's not entirely a bad thing. What is a bad thing is context-sensitive help in Windows programs died with the format -- HTML help has never been integrated into applications in the same way, and Windows applications are the poorer for that.
It has been possible to download a Microsoft utility program to view .chm files in Windows versions from Vista to Windows 8.1. There is apparently no equivalent utility for Windows 10.
See this Microsoft Knowledge Base article.
That doesn't help if you have an old application with good WinHelp help but can't view it under Windows 10, of course.