How can I toggle back and forth from a main pdf to its attachments?

I have a main document that I created in word and inserted hypertext to either link to 1) websites 2) a series of appendices, 3) 6 large format pdf maps or 3) a series of reference documents.
In Word, I have everything in a thumbdrive directory with the main file and three folders holding the individual files of the maps, appendices and references. All the links work but the file can't be copied to another drive without redoing all the links to the files (there are about 40 files all together).
I saved the word main document as a pdf. All the auxiliary files are also pdfs. All the weblinks came through in the pdf of the main document but the links to files need to be re-established.
1. I tried to create an acrobat portfolio with the main file and the folders of maps, references and appendices but I can't seem to make links in the main document to open up specific files in the folders.
2. I compiled all the files together into a binder and tried to use bookmarks to link the main part of the document to the first page of the 40 supporting files but at 700 pages the document is just too cumbersome to recreate the ~100 bookmarks I would need to add.
3. I tried adding everything as attachments and created links but once the link is activated from the main document and the new window opens, the main document has closed up. I need the reader to be able to toggle back and forth between the screen with the main document and the supporting documents.
What I am trying to create is one main document with links to the maps, appendices and references that will open a new window when each link is activated. Then the new window can be closed and the reader is back at the screen of the main document on the page with the link they just used.
This doesn't seem to me like it should be difficult since it almost works in Word except for the file structure.
I would really appreciate any guidance on how to make this work. The document and supporting files have already taken more than a year to put together and I'm stuck at this last step.

I think that the number of clicks to open a file is a rather shortsighted way to compare two operating systems.<<</div>
Well excuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuuse ME!
I happen to think it's a pain to click twice on files when I'm used to clicking just once.
But Tiger is a nice operating system. I enjoy that it has much more capabilities than the OS9. I mean, Tiger keeps up with the advancing internet. My beef is really against OS9. I can open OS9 in Tiger but not Tiger in OS9.

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