HOORAY!!! Another visitor to the land of the rising sun! No, wait… Another two visitors!!! Congrats @spacetravelmadeeasy and @jonesy_op!!!
And what an incredible time of year to visit. Autumn is without doubt my most favourite season! (I still got away with shorts in the first week of December mind!)
A friend of mine is planning to come over in the (brutally hot) summer and I wrote out an itinerary for him, you’ll be able to get things from it too but I can’t seem to upload a photo. I’ll see if I can do it later; unless my fingers get carried away with excitement!
Ok, prepare for massive amounts of info friends!
Firstly, you’ll need a Japanese rail pass which you can pre-order in your country from this website https://m.japan-rail-pass.com/
This is essential. You’ll pay through the nose without it. Although it only gives access to the slowest Shinkansen it will get you everywhere.
Have you thought about Horoshima? It’s very far away from the Kanto region though.
Kyoto for three days is perfect. The wife and I holidayed there for the same amount of days and it was just enough. The train station is a thing of beauty. You’ll have to see the Golden Temple and I highly recommend one of the finest examples of a Japanese garden on earth - The Ryoanji. It’s worth the bus ride and definitely go after the trip to the Golden Temple on the same day, they’re pretty close. There’s a famous fish market which has great food and not just of the sea swimming variety. You have to visit Fushimi Inari-Taisha - it is amazing!!! First place I went! In the evening you should dine outside by the river in a traditional Japanese restaurant. The reason I say a traditional Japanese restaurant is because there is nothing else like it: unparalleled service in a way that the Japanese enjoy. This river should be strolled along after your meal. It is also has wonderful photography spots.
Osaka was ok for me but I never thought anything was cheap. Especially the current second to Tokyo in Japan.
In regards to your stay in Tokyo - you are going to love it! It is big, busy, and bustling. It’s at the end of your trip, right!? I’d advise tired feet to start more relaxingly and venture to the wonderful Odaiba. This bay area will bring you the wonderful sights of Rainbow Bridge and the joy of sand between your toes and amazing photo’s to your camera roll. The shopping mall is terrifically placed and has equally great eateries on offer for all food types. Traveling there by the sky train is a must.
I’d spend two days getting lost in Shibuya/Shinjuku/Omotesando Hills/Harajuku in no order. Akihabara is crazy and easily experienced however it is a bit further out from te centre.
Now, the all important synth shops. 5 G is a gangbuster-must! In Akihabara there is a synth shop but it was hard to find the first day I was there. It is above a Softmap Store. There are great directions on this thread https://www.gearslutz.com/board/electronic-music-instruments-electronic-music-production/283101-5g-tokyo-synth-porn-super-store-check-out.html
if my memory serves me correctly for both stores. The latter has great deals on gear. Both are ideal spots for a no problem with the wife browse.
I’m not sure who told you it was cheap and personally I’d eradicate that idea. The Japanese know their stuff. The only place you’ll find super smashing great deals is at a Hard-Off - a place which your wife will definitely not enjoy. I picked up a DX7 complete with DX7 flight case for ¥2000 but the battery was dead. They didn’t know so they hawked it off for peanuts. Plus, I scour because I live here. Another store that won’t get you in trouble is the Ishibashi near Manhatten Records. A great place that boasts historical synths with handwritten ‘Please Don’t Touch’ labels and as well as a cabinet of classic Casio’s and up to date gear there is everything inbetween. It’s probably my favourite due to the diversity.
I would start day one of my Tokyo trip with a Blue Bottle Coffee at the top of the street, walk and (window) shop the whole road and stop half way for a Starbucks opposite the Vivienne Westwood store and next to Bill’s inside the same building for a cake and another coffee. Then I would hit up 5 G. After that I’d pop across the road to the Meiji Shrine to make a wish and buy a tombolo future predictor thing for shits and giggles. Then I would go to Akihabara and do loads of fun stuff. Double back and go to Tokyo’s Blue Note to end the evening.
Another place that should definitely be visited is Yokohama. That is a future city if ever I saw one! The views and photography opportunities from the top of Landmark Tower will leave your flabber fasted and your awe struck!
I went to Taiwan recently and had a helluva time mostly thanks to the fact that my old work mate lives there. It’s so much easier when someone can lead you from place to place. No time spent looking at maps and arguing with the wife after you followed her directional skills that turned out to be wrong. Hahaha
Time is the biggest factor so spending it looking at maps ain’t cool. Not trying to beg friend but hit me up via PM’s and lets see.
Food. 
I’m a massive foody
You need to go to a Yaki-Niku. They offer an ‘All you can eat’ and ‘All you can drink’ deal or just one.
You need to eat great ramen (there is also as low as OK, I’m sorry to say.)
You need to eat Udon with tempura.
You need to eat
And I’d go to China Town in Yokohama for food and a great experience after walking around Yokohama for day.
Japanese people lack a certain idea of first world survival in my opinion which can only be good from a tourist point of view.
The 7/11 coffee is amazing! Cheap with great beans - it makes me scratch my head!
I think, after two long sittings and thoughtful consideration, I’m done for now. I will have probably missed stuff but I’d sign this off as Holy Grail for now. 
