I would dual boot ubuntu and xp (Thats what I have)
as for ubuntu running xp/vista/mac programs, ask your friend what he did to get all of that working (I have wine which is a windows 2000/xp/vista emulator and have yet to get more than 1 program working)
oh and I was able to install directx on my machine, not sure if it worked as I have yet to get a game installed.