alt Hacker NewsOrthography is probably the biggest stumbling block going back to the 1500s or 1400s , but that’s really because the rest of the language has changed in vocabulary and style, but is still understandable. If you think the 1200 or 1100 entry are mostly orthographical changes then you are missing the interesting bits.
I would prefer to see a version that was skillfully translated to modern orthography so that we could appreciate shifts in vocabulary and grammar.
To me, it is nearly like trying to look at a picture book of fashion but the imagery is degraded as you go back. I'd like to see the time-traveler's version with clean digital pictures of every era...