Note that the NYTXW is not the only crossword publisher out there. I construct crosswords from time to time, and I always send my best puzzles to the NYT first

Note that the NYTXW is not the only crossword publisher out there. I construct crosswords from time to time, and I always send my best puzzles to the NYT first, simply because they're the most prestigious and pay the most. (And you can't send a crossword to two publishers at once.) On your other note -- it's really not difficult to make a bad, or even mediocre, autogenerated crossword using pretty simple software. There's several free or inexpensive programs out there (I use CrossFire). The main obstacles for AI-generated crosswords are: (a) the "theme", the 3-5 longer answers that the Mon-Thu and Sun puzzles are usually centered around, most of which involve wordplay and misdirection -- it's possible, I'd like to see an AI reliably come up with those. (b) the clues, though I don't think these are intractable either.