3rd Gen iPod Touch & Best "syncing" methods

my first gen 32GB iPod Touch recently bit the dust and was replaced with a 3rd gen version and I thought that "backing up this iPod" would back up apps, etc. but just backed up the Notes and some settings within the iPod.
Which I found out when I restored it to the new iPod, not to mention everytime i connect the new iPod with the restored version of the old iPod to itunes it always says it "crashed" yet I have no idea what exactly crashed even looking at the logs.
So i wanted to reformat it again and start over with being able to back up the Apps. My only dilemma is that I use multiple systems through out the day.
At home i have my 27" iMac with my main iTunes library attached to it and drag & drop music to the iPod.
And a 17" MacBookPro at work that i bring my external drive with to put music on the ipod and the itunes library there.
I have only ever used manually manage my iPod for music & media. So this whole sycning process is somewhat new to me and trying to get a best possible way to get it done.
Basically I wanna still be able to drag & drop music to my ipod from both Work & Home Machines.
But I also plan on syncing Applications & Calander since I realize that they dont back up during a Back Up process in iTunes & syncing seems to be the best method.
I just dont want it to erase my Apps & Cal info when I plug it into my work machine which has different Cal events and I want to download apps on itunes at work machine as well.
So is there a way to include both Work Cal & Home Cal info.
AS well as add apps from the work machine & the home machine?
Thank you!

maybe this KB will be helpful.

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