My path has been to stay on windows but go to open source applications.

• Audacity is my sound editor.
• Open Office is my word processing program. As of 3.1 this really shines. Even some of my non-techy friends are starting to use it. However, if Word were $50, they would not.
  
• VLN is my video player
• Azureus is my torrent program
• Cdisplay is my comic reader
• Avant and AVG are my virus scanners
• Firefox is my browser (with noscript, adaware, and the video capturing helper) and radio station player.
• GIMP is my graphical editing program.

The main commercial software I own is Dragon Dictate. But... I lost the disk and now can't reinstall it (for months). I went back to buy another copy and they'd raised the price 50% which was irritating. But there isn't a good voice recognition program yet. So for now I make due and rub my wrists or bring up my laptop which still has a good installation (yup. I bought two copies of it-- my wrists & forearms were that bad at one point but massage and curls with 20lb dumbells have helped a lot)

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When I go to UBUNTU or another version of Linux, it will mostly be an afterthought. For now, I've experimented with the LiveCD's (which some banking people are now recommending to avoid getting your identity rippped off).