Put PCLinuxOS on an old desktop a couple months ago. The *only* times I’ve had my XP machine on since have been for either ITunes or Quicken. I am an ordinary, non-geek user.
I just have my music collection as mp3's and use amaroK to manage it. Several thousand songs without any issues.
Check your repositories. Ubuntu has iTunes connectors now. And there are multitudes of Quicken clones, also. I have a Windows Pocket PC Phone. Still, no way to connect it, which is to be expected since it’s a 2003 or 4 model release.
I go here and read a lot LOL. You might want to give Salix OS a spin sometimeits great on older hardware. I think they have a live version on their homepage but most you find are install disc PC Linux is a great distro might not want to change!