Filename and path sizes and characters

I am failing to load 4000+ tracks to my Ipod from my XP machine using Itunes 7.50.0.20. This is an Ipod Clickwheel 20GB. I want to load 17.86GB in the now empty Ipod. However it gets so far then stops saying there is not enough space.
I wonder if am I getting the wrong message?
Some of my tracks have very long filenames/paths e.g 124 charactere filenames and 213 character paths. I also have some filenames with " (double quote) in.
Could this be the reason?
If so what characters must I avoid and what size should the filename and paths be limited to?

Filenames and paths are irrelevant. They are renamed on the iPod anyway.
20 GB is not really 20. It is a rounded number all HD manufacturers use. Plus you lose some space due to formatting and the iPod software. There is also meta data for the songs which takes some space.

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