I use my own notebook for most of my work but recently took on a new contract role that included a work notebook. As I use my iPad for meeting notes and recently on an interstate trip found that I did not need my notebook until I got home (might be able to travel lighter!)
In any case I need to be able to sync with both notebooks so that I can manage the various documents I generate.
For me I have previously done something similar when moving from an older system to a new system and simply copied the iTunes folder from the My Music directory from the old to the new. This morning I ensured that I had both systems with the current iTunes and then sync’d my iPhone and iPad with my personal notebook. I then copied the iTunes folder to the new work notebook (having renamed the newly created iTunes folder to iTunes.original just in case). Once that was done I plugged in my iPhone to the new notebook. iTunes prompted to transfer Purchased Apps which was ok, and later I agreed to Authorise this computer using my regular account in the iTunes store. Once that was complete, I did the same process with my iPad and it all works. To confirm that I had no issues I then did a repeat sync with my personal notebook which also worked. Sync’ing with two notebooks works.
I also read with interest this entry from Andrew Grant’s ‘Shiny Things’ blog and I will want to investigate this further.