In the case of software that should run but doesn't, you should blame the developer rather than Microsoft. Microsoft is usually clear about what won't be supported in future releases of Windows. Unfortunately, some developers do it anyway. As for dropping 16-bit software support in 64-bit versions of Windows, I suspect that the number of people running 20 year old software is rather small. There comes a time when we must recognize that the return on investment too small for Microsoft to continue offering support. In those cases we are usually stuck finding third-party solutions and even paying for it on our own.

I do agree with the relearning the interface bit though, yet even then I have to acknowledge that Microsoft has very little choice here. It is very difficult for them to sell a product based upon it's technical features to an audience that doesn't understand those features.