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I installed Leopard on my iBook yesterday. It went pretty smoothly. First I transferred all the files and settings to the Leopard iMac. I downloaded all the applications, which I purchased in the past, to make sure I had the right versions. I also downloaded the corresponding Application Support files, so I have once again the right settings. I needed to do some extra work on transferring AddressBook and Mail.
Then I started TimeMachine on the iMac to get a good copy. In the mean time I did a clean install of Leopard on my iBook. And once that was done I did an upgrade from the TimeMachine backup. That went all very smooth. Only my iBook thinks that it is an iMac. The saved window positions assume a larger screen for instance. More troublesome is that the iBook assumes that it has a french keyboard, which it doesn't. Have not found yet how I can correct that system-wide.