The sakuras may be in bloom too.
The sakura bloom forecast will be available March 1 here http://桜.jp/
The best time for crab in Japan is December to March, but not the best time to go touring Hokkaido (Sapporo isn’t that cold by North American standards, by the way - more or less the same as Chicago) unless you just plan a couple of days of eating and drinking, which is not a bad plan.
April is for all things sakura - sakura ebi, sakura tai (madai in top form), and also early (but already great) season for clams (akagai, hotate, tsubugai, mirugai… a bit early for torigai)
One of the most beautiful seasons is during the current week and the two following it. The weather is good (November 3 has been scientifically determined to be the least likely to be cloudy or rainy in the entire year, and indeed it was sunny this year, although right now it’s raining outside), the leaves are turning, you already get good sightings of Fuji, and between the matsutake, an abundance of white fish, milt (cod milt, fugu milt, salmon milt) and early mullet roe it’s very hard to complain about the food.
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Chicago winters are pretty bad. 
Thank you. Your responses have been extremely informative and helpful. It’ll be tough to miss Matsutake mushroom season in Japan but it looks like late March/early April it is for the shellfish and the cherry blossoms.
Any recs for good eats in Osaka? High end and low end welcome and all types of Japanese cuisine. Preference for seafood goodies.
May have to switch out Hokkaido due to logistics and distance.
I enjoyed my meal at the 1* sushi joint Hoshiyama. Note - it’s a Tokyo/Edo style sushi.
The food halls in Osaka totally smoke the one’s in Tokyo. Hankyu Umeda main store was the largest I encountered - totally overwhelming! The food halls in the other nearby departments stores are also worth checking out.
It would be a shame not to have any Kobe beef in Osaka.
Btw the Suntory Yamazaki distillery is located between Kyoto and Osaka. Japanese whiskey is 40% cheaper vs. purchasing in the U.S
For me, when I visit Osaka, it’s all about the sheer variety of street vendors and casual foods. Agree about the depachikas too.
For some nostalgia - check out Hokkyokyusei, the apparent creator of omurice. It’s just a block or two away from the famous Glico running man neon at the main shopping drag - Shinsaibashi.
Osaka:
I skipped out on this one, though my traveling companions went, but if you can have someone make a reservation go to Binbiya. It’s a one Michelin star “izakaya” (very high end at that) and has a fantastic sake lineup. The problem is that the menu is entirely in Japanese, or you can just have a tasting option then inquire with the waitress what’s on the menu. If you want to do uber high end nigiri, you can attempt Sushi Saeki which is considered to be the best, but they have apparently stopped accepting reservations from Japanese speakers for non Japanese speaking customers. We then went down the list on tabelog and hit up Sushisho Hirano (Air BnB host made the reservation for us no problem) and that hit the spot with really friendly and warm service, great food. Location wise not the easiest to find but we asked a local and he showed us where. Both are in the Kitashinchi area, lots of glamor (Japanese execs with kimono clad women) to see in the evening. In the area is Patisserie Gregory Collet which had a very nice selection including cheesecake and splendid espresso.
If you plan to drop by Kuromon Market, walk around till you see a bluefin tuna specialist vendor. It’s called Maguroya Kurogin まぐろや黒銀. Don’t bother with their chirashi/kaisendon, and just look at the blocks of toro. Pick the most expensive kind and splurge on sashimi. Aomori Prefecture Kama Toro. Get an order of BBQ toro too. If you have room, see if you can find the vendor near the main gate on the right, charcoal grilled Japanese saba.
Isomaru Suisan 磯丸水産 is a chain also in Tokyo, but you will find a 24 hour branch at Dotonbori. Be very selective since quota is precious. You can get a large maguro grilled collar, but I would recommend trying some BBQ (grill at the table) clams, scallops, and horned turban shell (sazae) fresh from the tank. Do not miss the kani miso which they serve a humongous dollop inside the crab head, it’s freaking heavenly after BBQing. It could be a small Matsuba gani but it also looks like a Seiko gani as well. A mug of beer and you are set.
Dotonbori, just try any takoyaki vendor where there is a line. If you see Osho Gyoza, it’s worth trying (make your own dip sauce from chili oil, ponzu, garlic). If you see the Kani Do Raku flagship store, only get the charcoal grilled BBQ snow crab legs (Matsuba gani). It’s done medium rare and ridiculously awesome (though sometimes hard to extract form the shell) and any souvenirs you might want. Do not under any circumstances go inside the restaurant to it (tourist trap).
Osaka’s Takashiyama department store basement is heavenly for foodies like us. Packaged fish porn heaven, from fresh sashimi to himono (dried fish). The jarred kani miso is heavenly, and I brought a few back, one of which Mori Sushi used up for making their kani miso sesame tofu (which I kind of regret since I only got a small piece). Around 700 to 800 yen a jar but supremely high quality. Check out the sakes and you might be able to taste.
Ramen: too much good stuff. We loved the location of Kinguemon ramen 金久右衛門 where we stayed we went 3 times. 500 yen a bowl and it’s freaking gold. These guys were 3 year champions in the running for their shoyu ramen (and even have multiple variations of this). But I’m sure anywhere you go, it’s good. It’s a chain, but it blows away anything in California.
Our Air BnB host took us to his favorite neighborhood yakitori/izakaya called Tori Nabe Tei とりなべ亭 • トリナベテイ, 5 to 8 minute walk from Teradacho station in the Abeno Ward area. Splendid chicken sashimi and the chicken hotpot/tori nabe was out of this world. Solid yakitori, and frosted mugs for beer.
I think you’ll find there’s been a major shift in Japanese whiskey pricing. Imagine you’ve been producing limited quantities of it for years and you suddenly win all kinds of international awards leading to every last drop of 21 year old whisky, and almost all 17 year old being bought up… your only way forward is to start selling much younger whiskys for the same price, or more 
Shopping at the airports was terrible, basically wiped out of older bottlings. I still had success finding 17yr Hibikis in the city liquor stores.
If you care about Michelin, there is a ramen place just received one star.
Trip Update.
Reservations made for Binbiya osaka. Going with Chef’s special with a request for extra seafood due to them being Japanese speaking only.
For Tokyo, notified the concierge and they will try to get us reservations at Kondo, Sawada, and Yoshitake.
Once we get those set then will fill in the rest of the dinners and lunches with Izakaya and yakitori.
Any other recs for izakaya or yakitori in Tokyo?
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Good man!
Bibiya Japanese reviews and more importantly, photos
I envy the opportunity to try so many unique Japanese sake that will never be properly imported to the USA.
e,g. Isojiman non export versions
If the r.gnavi menu listing is of any indication of what they regularly offer, there are tons of awesome looking dishes. Copy and paste into google image search to give you an idea what it is
いわし梅煮 looks damn interesting (iwashi ume-ni ?) Japanese plum braised sardines…
牛すじ味噌煮込み - gyu suji miso-ni (braised beef and tendons in miso stew)
Grilled shirako
Makes me wish I didn’t skip out on Binbiya…
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Nakamura is a non-smoking Izakaya. Food is quite good. Recommended by Robb S. of Bento.com. We went there in November. It is a busy place, even on a Tuesday night. Reservation is highly recommended.
You’re going to hate it even more.
I requested kani and nabe and just got an email back from the concierge saying that they can offer us tecchiri nabe which is fugu and apparently an Osaka specialty.
Thanks for the rec @beefnoguy.
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The company that operates Nakamura designs and launches Izakaya as a business. Some of them remain company owned (like Nakamura), others are independent and just share many of the design sensibilities. Easily the best of the bunch is Kotaro in Shibuya. No English, but they’re happy to offer a very satisfying set course menu with excellent Sake.
Got shut out of Yoshitake and Ishikawa. 
Are you still on for Spring?
Maybe I’ll meet up with you there. I am planning on having some business to attend to (ahem) in Tokyo during cherry blossoms…
March 30-April 3.
Let’s do it.
Make us a res for sushi (concierge failed). We’re a party of 5