Re: Do I need a custom shipping module?
Yes, you'll need a custom module - none of the standard ones will do that for you. You will need to modify the product edit pages in admin and either add a field to the products table or add a new table (a new table is the best approach for future upgradeability). You might be able to get away with using the existing attribute weight capabilty to specify additional shipping.
If you've not worked with PHP before, you'll have a steep learning curve - but your previous programming experience should help to at least develop the required logic flow.
Neville
An assumption is what you arrive at when you get tired of thinking...
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