Way I hear things, Apple hasn't completely gotten rid of Carbon yet. iTunes is still around, in all it's terrible glory.
I primarily use windows, but I have a virtual machine with Linux specifically to run Sage. I know its not the same, but it is a very similar concept.
tl;dr backward compatibility keeps customers, no backward compatibility makes them flee, for Windows.
What Apple products are we talking about here? Are you implying that people who own mass market consumer electronic devices like iPod and iPhone are more technically inclined? I think that is an inaccurate statement: it is nearly impossible to hold the kind of market share in that space and somehow do it with only (or even mostly) "technical" users... there just aren't enough of them. Not to mention that it flies in the face of Apple's "it just works" marketing mantra.
In the world of PCs, you might have an argument. But I would say, once again, that your assumption goes against everything Apple marketing has been saying for 10 years. If the marketing has been working, then they've been attracting non-technical users into their user-base for years.
"[...] as Windows's featureset is much smaller than its competitors' [...]"
In what way?
The problem is that Microsoft used to say no as well. The larger the (software) company is the less humble and wise it becomes as its realizations are stretched across multiple divisions.
The only way to be free of artificial restrictions is to use OSS.
The only way to be free of artificial restrictions is to be technology agnostic, to not subscribe to any one camp for religious reasons, and to simply use the right tool for the job.