I have no issue paying for software...I use commercial, shareware and freeware. I'd go Mac but I have too much tied up in hardware and can't justify the changeover. However, I can continue to use existing boxes and peripherals if I make the switch to Linux. (I'm soon to put a Linux server online.)
Since I do a fair bit of web work, I need tools such as CoffeeCup. I'm not going to mess around with having dual booting systems...too wonky for an office environment. So I'm stuck with Windows.
To stand momentarily on my soapbox, I always believed (and I've been a PC user since 1983) that Operating Systems are a language that really shouldn't be owned by anyone...similar to no-one owning English, or German, or Mandarin, etc. But someone might own the book or magazine or whatever that was constructed using the language. And that is what I would pay for.
WIndows is a pig (VISTA a complete disaster). I want to work with tools in a language (say Linux) that is safe, completely free of handicaps and hassles, and allows my tools/software to work properly.
CoffeeCup -- even though I have purchased the complete CC software line (Windows) I would pay a fee to have my software ported to Linux. I don't suppose there are enough customers like me to make it worth while though.