I had a thinkpad that came with Vista, and after using XP for a while, I switched it to Ubuntu 10.04. I really like the OS, except for two things: installing software could use a nice GUI, and Gimp. Gimp was the deal-breaker ultimately. I need a solid image editor for my RPG, and Gimp is not a lateral replacement for Photoshop. Switching from Word to Open Office was painless, but not from Photoshop to Gimp. I now have a ideapad running Windows 7, which I like well enough. If I had a second laptop, it would run Ubuntu for sure. My second laptop with Ubuntu recently died. Hubski runs on a Ubuntu server. btw, I can't believe you're still using ugly hubski, /. :)
Have you considered running Photoshop from a virtual machine on Ubuntu? I do that with Powerpoint when I need it at uni. Photoshop Portable runs under wine, be it with a few minor bugs here and there. I left Windows for good 2 years ago, when I was introduced to Ubuntu at uni. Now using Windows just frustrates me to no end. Unless it's Windows XP. Never liked Vista or 7... let's not mention 8. I have no regrets!
Ah yeah, proper replacements for photoshop and flash are the major reasons my wife doesn't switch as well. I have all my computers dual or triple booted with Windows, ubuntu, and haiku at the moment; I love trying out new OSes. And I will use ugly hubski for as long as it's available! I stare at enough Courier New all day anyhow it doesn't really phase me anymore.