Personally I find Virtual Box to be the most user-friendly but if you
are needing USB support then don't get the one in the Ubuntu Software
Centre - go to the Virtual Box web site and download from there. Note
that you'll need a valid WinXP COA to install WinXP and it's also
going to need AV protection but for the envisioned use any of the free
ones will be sufficient.

Alternatively - there are ways of working Apple music devices without
iTunes :-)