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If a user clicks on New from a document library then a word template opens with metadata in the header section, will the SPServices jQuery cascading dropdowns work in the word's header? I doubt it. If not, can I force user to fill out the metadata first when they click on new then open the word template in the word and it should be filled as user already filled the metadata?

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You should get your accept rate up. – Abe Miessler May 19 '11 at 17:49
@Abe: Okay, I have gone through my posts and accepted answer where I could. How am I doing now? – Roxanne May 19 '11 at 18:43
Much better! :) – Abe Miessler May 19 '11 at 21:17

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No, because the SPServices Cascading dropdowns functions on list forms. To my knowledge, you can't specify metadata before creating a document. You could require check in/out on the document library to force an item be checked in before being available and this would let you use the SPServices cascading dropdowns since that's effectively an editform.

I'm wondering if there's a way to extend the document information panel in Word to account for something like that.

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AFAIK, Document Information Panel can be modified only with InfoPath. Neither SPServices, nor SharePoint Custom Field Types can help here. Another place where they will not function is DataSheet view, because it is an ActiveX control. So, you should remember this when planning to use cascading dropdowns or any other fields customizations. – Andrey Markeev May 19 '11 at 18:55

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