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If you're getting errors with 1.5.5 then I think Dave might have to help you figure out what's wrong.
If practical, you might want to do a clean install of Leopard instead of attempting an upgrade from Jaguar (if that's even supported -- I dunno) after you've got a backup. Not sure if Migration Assistant from 10.2 to 10.5 will work, or how well.
Years ago I first installed a major OS X update on an external drive volume, booted/configured/ran that for awhile, and when satisfied it worked cloned it (with SD!) to the internal drive volume. I never rebooted the older OS as needed, just copied over files to the new OS as needed until leaving the rest behind when overwriting the internal volume (which I also kept a sparse image backup of for awhile but never needed anything from it).
So, something similar would be another option for you though obviously more complicated.
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