Hey Robin, I'd definitely start by taking the above advice and clearing out any extra .deb files that are lying around in the cache--that could free up quite a bit of space.
I upgraded a couple of installs from etch to lenny a few days ago, and it took about 1.5GB of free disk space to download and unpack all of the .deb files I needed. I had always used apt-get prior to doing this upgrade, but read a recommendation suggesting aptitude was better at resolving dependencies, so that's what I used and I've had no major issues. (Actually, I'm starting to get addicted to aptitude's curses interface. :-) Rick.
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