Is Acrobat X Pro suitable for publishing an interactive book (as a PDF)?

I am evaluating Acrobat Pro X as a possible vehicle for publishing an interactive reference book (a numismatic catalog).  The Bookmark capability of Acrobat is particularly attractive because the Bookmark panel functions as a very convenient and intuitive interactive nested Table of Contents, and bookmarks embedded in an alphabetic list at the end of the book could serve as an excellent, though labor-intensive, index.  If my master Word document (about 400 MB) already contains a linked Table of Contents and Index, can that interactivity survive conversion into an Adobe PDF file?  If not, and I have to do all that work in Acrobat, can that functionality be saved when it comes time to update the Word master file and publish a subsequent edition?
The desired benefits of publishing electronically include the ability to make corrections and additions as they're discovered and then quickly to publish an updated edition quickly and easily.  (This ebook will be distributed free of charge.)  Is this feasible with Acrobat?
Thank you.

Thank you, George and Bill,
Right now, I do not have a single document.  The book currently exists as 70 separate Word and PowerPoint files, whcih can be printed as a single paper book.  What little opportunity I've so far had to play with Portfolios in Acrobat made me think that whatever problems I'll face would be simplified if I were dealing with a single file.  However, I do not want to compress the images any more than absolutely necessary, because numismatists value the ability to enlarge the image of a coin or medal for detailed study right down to individual letters and numbers in the inscription.
Since size will be a potentially significant factor, perhaps debilitating, might it be better to approach this challenge with a portfolio?

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