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There was a post not too long ago, where someone reported that they'd done a lot of upgrades, some even beyond what you describe, and they didn't seem to think it was overly problematic. You can easily upgrade whatever you like with Synaptic, though you'll want to add some Squeeze repositories, I'm sure - just be ready to try again if something isn't compatible. If you look in the appropriate forum, I'm sure you'll find the upgrade related discussion.
Cheers!
Krishna
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The nice thing about the thumb drive install: it is already compressed for easy backup to hard disk before booting for an upgrade session.
However, my hard drive install is what I am thinking of heavily upgrading. The drive already has Grub installed for dual booting into Windows. I did something kind of cool. I followed the instructions to install Clonezilla on my hard drive. It worked first time!
Now I have a Clonezilla item on my Grub menu. It makes an iso image of the Knoppix partition in 4 minutes including boot time. Then I reboot into Knoppix for upgrades.
Slow progress. I'll look for that post.
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