That's because the exchange for a lot of OS X stuff is: You pay a small sum of money in exchange for developers that work their asses off on making your user experience perfect. Delicious Monster, Cultured Code, RealMac, Blacktree, Panic Inc. - especially Panic Inc. Then there are the developers who don't make commercial Mac apps but who are part of the same developer scene: Coudal, 37signals, Neubix, on and on.
They're actually why I bought OS X: Once upon a time, I used Virb - designed by Neubix - read their blog, and slowly came across these other developers and their blogs, and fell in love with all these small development teams whose lives focus on developing their applications and making a profit. When I got my Mac, I started with a few of those teams' applications. Specifically, I bought Panic's Coda and demoed CC's Things. The experiences I get with those applications are stupendous.
Coda's the only thing I use that makes me love coding; without it, I get bored easily with the processes. I'd say it's absolutely been worth my $100 purchase. A hundred dollars for a code editor, FTP transmitter, CSS styler, a set of well-formatted reference books, and in-app browser testing? That's a damned good deal. And yes: I can do that for free, I could open emacs next to Safari, download free guides online. But it's worth my money not to ever have to bother with that stuff at all.
The license agreement... I don't find the license agreement at all frustrating. You click "Accept" once, then never see it again. MobileMe I got almost immediately: It syncs up everything I've got, gives me a nice email system, and it's worth the money I pay for it. I've seen the free alternatives, and they're not worth paying money for.
As for the "trivial bits of software", I've found I need very few applications to complete my Mac experience. I used the free OnyX to tweak my settings, I got Dropbox, and outside of Coda and iWork I find I rarely need anything else. I used to use Fluid.app to run web applications I liked, and that was free. Max converts every file format I need converted, excepting WMVs which I can convert using iTunes in a virtual simulator, and I need to convert WMVs very rarely.
Some people need free. Some people think that everything should be free. They're absolutely allowed to go that route. But most Mac users don't find it outrageous to pay developers for their time. A hundred dollars for a product is nothing, when that hundred dollars ensures never once having to look in a help manual to get something done or dealing with a crash or a slowdown or anything, really. It's similar to the thousands of dollars spent on the Mac itself. You don't pay that money for the RAM, or the screen. You pay that money because Apple tries to guarantee that things don't fuck up for you, and the impressive thing about Apple is that things really don't fuck up. I've been on my current set-up for a year and I've had five total crashes, each from weeks of multitasking processes without ever putting my computer to sleep. I have no problems that I can't find an app for. A lot of things on the Mac are so simple that I now have problems using Windows and Linux because they can't handle the functions that I use now. So no, that doesn't bother me, because for my money I get trust. Working with Ubuntu bothers me, because things don't feel like part of a logical whole. It's a matter of personal preference.