It’s not about you. It’s about how should Microsoft move forward, and how long should they support older tech because companies don’t prioritize migrations from older technology.

One of the major issues with Windows has always been that they have hack on top of hack to keep backwards compatibility. You can read Raymond Chen’s MSDN blog to get an idea of how bad it is.

The answer has to be somewhere between Apple - not long enough to be appropriate for the Enterprise - and too long in the case of Microsoft where it slows down development, causes an increase security vulnerability surface, and causes Windows to be a resource hog compared to other operating systems.