At least without the App Store reviewers crawling all over everything you do, putting an enormous level of scrutiny over everything you do. And the functionality has to justify it (not that it should operate without it, but with it has to validate why -- is it using some massive cloud resource to guess your next word, etc?)
That he ever got away with it was during confusion over keyboards on the watch where they weren't officially sanctioned and thus policed.
But otherwise he's engaged in building features for someone else's platform. Eventually those features get first party inclusion. This is the surest thing in this industry, and people comparing it to sherlock, etc -- ridiculous. Apple made a larger Apple watch so they decided it's time for a keyboard. That this guy is trying to claim some sort of moral/intellectual ownership over keyboards and/or swype typing is ridiculous, and it's the sort of overreach that is usually criticized viciously on HN.
And if Apple truly made an offer to "buy" his keyboard, it was certainly just to settle bad blood. The likely outcome would have been that they toss his solution and then do exactly what they did, which is build their own.