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 makes it really not worth that kind of money to us. I'd been tracking this periodically over the past few months and never saw any great deals jump out at me so we decided to book with points.

Between Sapphire and Amex, you can transfer to nearly every airline in existence. On one hand that flexibility is awesome, on the other hand it's a bit of a nightmare to search for flights in so many places at once! Add to that the fact that I didn't have enough miles for two round-trips in any one account and it gets a little complicated. 

Here are a few random tips after finding the tickets:

• ANA still has the most complete search results for Star Alliance rewards. United hides certain airlines from the results (Singapore, LOT) and Air Canada's Aeroplan almost never offers a direct flight at the saver redemption level*. 
• BA's website only shows partner availability if there are saver seats available. I could imagine them changing this once their new peak/off-peak redemptions go into effect in April. 
• BA Travel Together certificates are useless if you're a North American going anywhere other than London. There's basically no availability of reward seats on anything other than the super busy NYC-London routes. 
• There's heaps of Japan Airlines award space right now via British Airways, but only in Premium Economy.
• Chase Sapphire has amazing customer service. The agent had to jump through a bunch of hoops to transfer our points from 3 separate accounts (mine, his, and my work card's) and even when we encountered some trouble, they were stellar in handling it. 
• If you're using Chase/Amex, Don't transfer points until you're ready to redeem, and if you see a lone, perfect reward, make sure you check here to see if the point transfer will be instant. Whereas our Aeromexico reward was long gone by the time the points arrived 10 days later, this time I had an instant transfer to Aeroplan and snagged a unicorn – two Business Class seats on a direct flight from NYC to Tokyo on ANA for 75,000 miles + $100 each! (hence my * above!)
• It's often worth it to create a frequent flyer account with a foreign carrier and then transfer points in to their program before you redeem. Many of them have a much larger reward seat inventory for their own customers versus what they offer to alliance partners for partner redemptions. In this case we were able to transfer Chase points to Korean Airlines, where there was a ton of First class seats available on their A380 service to JFK, so we did that for 80,000 points + $75 each.
• Most Asian airlines only let you book for yourself and selected family members. Officially adding family members to your account can take several days/weeks so this up early! I created a separate post about adding my husband to my Korean Air account.
• Many airlines require you to show the credit card used to pay for the flight, so make sure you bring it with you to the airport!
• Many airlines block partner redemptions for international First Class, so this is another advantage to having an account directly with the carrier. For example, Delta lets you book reward seats on the same Korean Airlines flight we got, but only in Business Class. Once our points were in Korean's system, we had access to their First Class seats and there was a ton of availability. Singapore did the same thing when they launched their suites product.
• I really wanted to do ANA First, but ANA's site only lets you do round-trip redemptions and I didn't have enough Amex points for that.

SO YES! WE HAVE TICKETS! ANA 777 in Business Class NYC-NRT, coming home on a Korean Air A380 in First from ICN to JFK. (We'll sort the flight to Korea once we plan the trip a bit more). I've never flown either airline before, so I'm excited! Toto Washlets and ANA's new "staggered business class" seats on the way there and Bimbim Bap in an A380 Kosmo Suite on the way back. 

If you look at the direct cents per mile (CPM) for this redemption it's 7¢ for the ANA leg and 8¢ for the Korean (the one-ways are $5250 and $6478, respectively). In reality it's less than half that since ANA round trip Business Class is pricing out around $5000 right now. But as I've mentioned before, valuing points is a tricky endeavor at best. Since the most I'd pay for that flight is $3000, you could say my CPM is only 2¢, but if I think about how much more fun the flight will be in an A380 in First, it almost becomes almost priceless.