I like the idea of paid, high-quality Windows software, but I have to agree with you that it's a difficult thing to make work. Trillian makes a very high-quality, and very Windows-y (in a good way!) IM client, and tried to go the free/paid route, but recently ended up adding ads to their free version, presumably because the paid version didn't make enough money for them to be profitable.
I do however, expect that as Apple becomes less and less of a computer for geeks (of various types) and more and more of a mainstream competitor to Windows PCs that it will suffer from more of the problems you outline. I've noticed that my non-techy, but Mac-owning friends don't perceive the different between Mac and Windows software in the same way that I do, and many of them also do a lot more piracy than I do. (I don't really pirate software except for Photoshop, primarily out of laziness.)
That is discouraging to hear. I've given up on the idea of being able to make any sort of living writing nice, general desktop apps for most any platform. Seems like you have to target a niche with a quality product so they'll have a need and a lack of mediocre competitors. No offense, but FOSS has done considerable collateral damage via the second point. Usually people would rather put up with a crappy UI from 1990 if it's open source than pay $2.
The gamer demographic on Windows is also a bit notorious for piracy.
I do however, expect that as Apple becomes less and less of a computer for geeks (of various types) and more and more of a mainstream competitor to Windows PCs that it will suffer from more of the problems you outline. I've noticed that my non-techy, but Mac-owning friends don't perceive the different between Mac and Windows software in the same way that I do, and many of them also do a lot more piracy than I do. (I don't really pirate software except for Photoshop, primarily out of laziness.)