New Computer for Mothers Day, will this work?

I think I have this figured out but I want to see if you all see any problems that I might run into.
I will be purchasing a new laptop computer for my wife for Mothers Day, it will be using Vista. Her current laptop has XP. I believe she has about 20 gigs of music/video that she has purchased from ITunes and a tad bit she has copied from a few cds. I have done the search function and printed everyting "I think" I need to transfer over but the different O/S part concerns me greatly.
First of all, I had planned on just using her 60 gig Ipod to transfer everything but I also have a portable hard drive that might make it easier. Everything is stored in the default ITunes directory, so I was going to copy the entire folder from her current laptop to my portable hard drive. Then, once we get the new laptop up and running I had planned on downloading and installing the newest version of ITunes on to it and then copy the ITunes folder from the portable drive onto the new Vista based laptop....this is where I'm slightly concerned! Will the difference of Operating Systems cause any issues?
Lastely, if all goes well as stated above, I have no reason to leave the music/videos on the old laptop so I will deauthorize that computer and authorized the new one, or atleast I think that is a good idea.
Is there anything I need to do with the Ipod itself during this process or should everything go well? My biggest concern is using Vista, I have heard nothing but problems but unless I order a computer from someone like Dell and choose XP that is really my only option...
All suggestions are welcome.
Thanks in advance!!

Everything is stored in the default ITunes directory, so I was going to copy the entire folder from her current laptop to my portable hard drive
To elaborate, make sure you copy the entire \My Docuemnts\My Music\ iTunes folder, not only the iTunes music folder.
In Vista, the iTunes folder is installed in Music (not My Music).
Simply replace this folder with the one you copy from XP to the external.

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