3 people, 3 different ways of getting to Japan

UPDATE: We're back! 

• Turns out we ended up arriving RIGHT as peak cherry blossoms happened 
• Tim's United 1k status got him a surprise upgrade to ANA Business Class at the gate 
• The 27 hour layover in Taipei worked out perfectly

Japan is finally open for real again, and we'd love to go back (it's where the 3 of us met, actually!). Here's the constraints I had looking for tickets:

• We've all seen the cherry blossoms before, so let's go AFTER the cherry blossoms but BEFORE golden week so we can avoid the crowds a bit.
• Try to go during Easter so we get one "free" day vis-a-vis Tim and Kelly's PTO. 
• Given Kelly's back and my recent surgery, get us there from New York in Business Class without paying the current going rate of $12,000 each round-trip. We were willing to do one stop if we could find a good deal.
• Given the similar time zone, shorter flight, and lack of health problems for Tim, get him there on a direct flight from Sydney in Economy/Premium Economy for $2000 or less. 

Given our relatively low points balances, how'd we do?

• I found Tim a direct round-trip SYD-TYO on ANA for $1440, including an optional upgraded meal service and an upgrade to Premium Economy on the flight home. (He's a United 1k and will earn miles and status points on this trip)
• Kelly and I looked for points flights and the only carrier with availability was United. We had enough United points between the two of us for one and a half legs (out of the 4 needed to get both of us there and back).
• Luckily United was having a "100% bonus when buying miles" sale, so for $1580, we bought the missing 79,000 miles we were short. So that gets us both there in Business, but how the heck would we get home? (Please note: I didn't click 'Buy' on those miles until I'd figured out a way home!)
• Historically, flights to/from North America to Asia have carried a staggering price premium for direct and 1-way flights (1-ways usually cost MORE than a round-trip!), so it seemed futile to even bother looking at a 1-way option home. But Covid changed the playbook for a lot of things so I hopped on Google Flights and miraculously it looked like EVA Air was selling a 1-way trip from Tokyo to New York via Taipei for approximately half the cost of a round-trip (≈$2600). 
• We LOVE Taipei and really wanted a 24-48 hour layover, but none of the options on Google flights let us stay long enough to go to a proper night market for some power grazing... Soooo off to EVA's website I went. It took a Lotta Buttonpoken (my new drag name!), but I was eventually able to get EVA to price out an open-jaw ticket with a 27-hour layover for the same $2600 price I was seeing on Google Flights.
• (Sidenote: I also manually priced out a flight via California on Japanese Low Cost Carrier Zipair, whose flights aren't in Google Flights. They weren't price competitive on any of the dates we wanted to travel, and doubly-so when you consider we'd have to get ourselves to California)

So in the end, two Business Class round-trips from New York to Tokyo, plus an Econ/PE round trip from Sydney to Tokyo for 321,000 miles and $8220. Seems like a lot at first, but given how full planes are (and ergo how high the prices are and how few reward seats there are), it sure beats the current $25,000 asking price for this itinerary. Using the ole' "cents per point" math, this came out to 5.5¢ – not too shabby in the current market.