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I think you can do this, but you're going to have use streams (and possibly a lot of them) with transition rules for each around probably clicked link. This feels a lot like one of those logic puzzles where you should write out all possible logical outcomes (streams) and then create their transition rules. I think this is possible (provided you can wrap your brain around this) but I think an easier work around might be to create a segmentation around what part of your funnel they're in (or use the modeler). Then serve up the content based around what part of the funnel and/or tailor the message. Although it seems like you want to base most of this off of what content they've digested, so that might not work exactly. (But hypothetically you might be able to create segmentations around what content has been digested, and at the very least, number of pieces digested).
I am not sure how scalable this is just because it seems time consuming to think of all potential outcomes. But good luck!