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.
There's been a recent heavily upvoted and profusely commented post about things people want to learn. It's close to having so many comments in a single day that it should probably have a part 2.
However, the subject seems to inspire thoughts about what *other* people ought to know, and while that's got a good bit of overlap, it's emotionally rather different.
So, what do you think other people ought to know? Any theories about why they haven't learned it already? Any experience with getting someone else to learn something when it started out as your project rather than theirs, especially if the other person was an adult?