I'm stereotyping a great deal here, but it feels like Windows users with a bit of expertise inevitably:

1. don't appreciate nice software (it's a rare thing, most programs are considered good if they don't have malware in them)

2. don't pay for software because they're 'smart' enough to use BT

3. don't care a lick about decent UIs because there's inevitably a free/open source program with that skates by on virtue of being free

The OS, as of Windows 7, is damn nice (though the terminal is terrible). The UI of the apps is almost universally bad -- most apps disregard the system UI theme for absolutely no gain, and they end up looking garish. Many apps that target the 'power user' demographic fall into a pit of endless customization, which presumes that users want to tweak their software using components written by random people on the Internet. It's as if no app on Windows is content to just do its thing, it always has to be striving to do more in a thoroughly mediocre fashion.

Your points are valid, but I think the percentage of inexperienced Windows users far outnumbers the users with 'expertise'. Those type of people

1. Do appreciate applications that "just work" and are willing to spend time choosing the right apps that suits them.

2. Haven't learnt of BT yet or even if they have, they're willing to pay to save the hassle of checking for viruses, trojans etc.

3. Do appreciate user friendly applications, they'll choose a better looking application with lesser features over a featureful app with bad UI.

Going after this crowd can be lucrative indeed, just ask patio11 ;)

Yeah, it just seems like it is hard to write an app that less-experienced users will both appreciate and use...much less pay for. After all, they may think MSN Messenger feels like it was written for twelve year-olds, but do they care enough to switch? Do they even know how to look for a replacement? (IM might be a bad example as nobody wants to pay for a client on any platform, it seems.)

OS X appears to simply have more of a tradition of independently-written, beautiful software.

Well, in most cases they want a real good reason to switch and the software must market itself as a replacement. Case in point Firefox and Chrome gained a lot IE6 users by

1.Having multiple tabs which is the killer feature

2.Marketing themselves as a secure and less-crashy alternative.

This might seem like an unfair example(not everyone has Google's or Mozilla's muscle) but the basics are the same for any type of software and given sufficient effort and planning, they can compete in competitive markets with established players.

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.

This definitely could sum up the majority of Windows users, but there are those who think differently. I for one am a current Windows 7 user who would easily pay for many popular Mac programs if they were available on Windows. Also, I'm very picky about design, though that's due to my Apple influence from iOS. And, for instance, if Things, Pixelmator, Billings, and several other apps were on Windows, I'd buy they and hold off switching to a Mac...