Well, I got it!
Post-trip UPDATE: Seoul to JFK trip report ! JFK to Narita trip report ! JFK – Tokyo in ANA Business Class for 75,000 Amex points + $100 via Aeroplan Seoul – JFK in Korean Air First for 80,000 Sapphire points + $75 via Korean Air My brother ended up canceling his plans for a party in Tokyo but doing Hanami in Japan is on the bucket list so we figured we should go anyway. This freed us to pick whatever dates we wanted/could find award seats for. For starters, we had about 200,000 miles each in United, British, Amex, and Chase Sapphire points. I followed my own rule and priced out the ticket on Kayak and the cheapest non-stop in Business was $5000 per person on ANA. That's well above my pain point :) If we were willing to do a 1-stop itinerary we could get the price down to a much-more-manageable $3700, but that would have meant flying on a North American legacy carrier. Their surly service, mediocre food/beverage options, and generally un-special experience