How do I sync my iPad to my external hard disk via two different computers?

I have my content on external HDD and I would like to sync the content to a single iPAD via a MBP as well as via a laptop.  But whenever I change the MBP to laptop or vice verse, the change is not transparent. MBP is not using the configuration created by laptop;  it will have to create its own configuration file (vice verse is also true).  There is lot of scanning of media and manual adding.  Is it possible to use iTunes the way I am hoping to use?  Or should I use only one MBP/laptop with one iPAD?

Using iPad or iPod with multiple computers  http://support.apple.com/kb/HT1202
Apps cannot legally be shared between Apple IDs - that is considered piracy.
However, you can legally install apps on multiple devices that use the same iTunes ID and are owned/controlled by the same person.

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