I did Apple for a number of years. They are even more aggressive in their "upgrade or perish" policy than Windows, it's a lot more expensive, and the OS isn't really all that different.
I let my software decide which OS I use. The StyleMaker app in Band-in-a-Box Windows has more features than its Apple app. It lets me write better aftermarket BiaB styles. Since that is part of my musical income, it requires me to have a Windows PC.
For years the styles weren't 100% compatible (they are now) so I needed to also have a Mac. The Mac required expensive updates. They went from Motorola chips to IBM chips to Intel, then changed to a version of Unix, and on and on and on. Each change rendered my existing software apps obsolete, and so they also needed expensive updates -- that is, if they were still in business.
If I had some software that I need to make a living with that worked better on Apple, I'd still keep up with Apple's upgrade or perish policy, but since I don't, I'll live with Microsoft's upgrade or perish policy.
Insights and incites by Notes ♫