Oh man, I wish I had links to some article about how much effort some MS engineer went to to get old versions of things like Quicken working. It was a good read, you'd like it, if someone else knows the one and can link.
Most of these stories came in the form of blog posts by Raymond Chen in his blog The Old New Thing. It used to be even more fun to read in its old form and layout, and I am fairly sure not all his posts survived the move to the modern "devblogs" platform. But many of his posts were published as a book by the same name. Highly recommended, and a great gift!
https://devblogs.microsoft.com/oldnewthing/
https://www.amazon.com/Old-New-Thing-Development-Throughout/...
Fairly widely read also by Joel on this topic: https://www.joelonsoftware.com/2004/06/13/how-microsoft-lost... (not the article cited on Twitter; links to Chen's posts sadly broken)