> [..] I can't imagine how useless an unthinking AI would be at this when my own family and friends who, and this is important, _know me_, can't find anything to get me that doesn't land in the above categories
This is precisely the problem - an AI does not really "know" the recipient (set aside of what it means to "know" someone). The result is you get something just a bit more varied than the usual "He's a Guy - he'll love some Whiskey Stones, a Bacon-of-the-Month subscription, or a Beard Care Kit" advice. (Adjust for whatever target demographic.)
This is precisely the problem - an AI does not really "know" the recipient (set aside of what it means to "know" someone). The result is you get something just a bit more varied than the usual "He's a Guy - he'll love some Whiskey Stones, a Bacon-of-the-Month subscription, or a Beard Care Kit" advice. (Adjust for whatever target demographic.)