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Do you own an Apple Mac well heres some software to convert video to the PSP/Ipod, heres the details:
VisualHub bridges the gap between numerous complicated video formatting standards, and people that just want to get the job done - just what you would expect from the Mac.
More info
Looks cool! FFMPEG for OSX is also very nice though. Easy to understand, and with batch-mode.
FFMPEGX (as well as it's base, ffmpeg), also has the keen bonus of being absolutely, 100% free. I checked out the more info page, and while it does look like this might make the whole process somewhat easier, my opinion is that you'd probably be hard-pressed to find something in it worth paying for.
I'd love to hear from anyone who's actually used it though.