Can't really offer much more advice. iTunes
should work with both iPods transparently. An iPod though can only be loaded with music from one computer – is there another PC somewhere?
Assuming both iPods are relatively new, they should both be able to use the same cable – so if one works with one cable, the other should work on the same cable.
I don't know much about Sony MP3 players, beyond that I know the software is crap. It should though be possible for the Sony software to be made aware of the music that iTunes has, and thus enable it to be transferred to the Sony.
Slow PCs seem to be a common complaint for people who use Windows.
My general advice which would fix all the problems you have mentioned would be to only buy Apple products.
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