The problem is that I know from past experience that fairly shortly after Microsoft “Ends” the life of an operating system then software developers stop writing software to work with it. The most problematic one I have found is that the tax software people will not allow their program to even install.
As for tax software, yowzer, yeah I see your point. I use an online tax preparer, FreeTaxUSA, for my taxes but I don't own a business or file long complicated tax returns. So I can see the concern there for those who do.