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paulfchristiano comments on Other people's procedural knowledge gaps - Less Wrong
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The phrases "generally no" and "generally know" both appear frequently in English. "it's a" is orders of magnitude more common than "its a." Replacing "know" with "no" doesn't significantly reduce comprehensibility--but it does make the phrase take longer to parse. Replacing "it's" with "its" doesn't reduce comprehensibility at all, nor does it make the phrase any harder to read.
There are a few situations where making a distinction can eliminate a syntactic ambiguity, as in "its fun"/"it's fun". There are also a few more where it eliminates a non-ambiguous but awkward construction, as in "it's its own server". And of course it'd introduce another kind of irregularity unless you got rid of the contraction apostrophe altogether, which might lead to some other strangeness that I haven't thought of yet.