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Linux
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You may want to check out Libreoffice Draw but with that many pages it may choke. You may also want to try out MasterPDF. That one is a paid option but you can try it out for free.
Yeah, Draw is too clunky for this. I've been looking at MasterPDF or qoppa's PDF Studio. I'll download Master PDF when I get home to see if the trial will allow for the functions I'm looking for. Thank you!