Osaka I enjoyed a lot more than Tokyo. Probably came down to the people - I found them a lot more friendly and accepting of foreigners - but also the geographics and in particular where we stayed. We were just on the outskirts of Dotonbori, about 8mins walk from Den-Den Town and Namba, etc. I had a lot more time to cruise in Osaka with less things booked, so while the family chose to have some total rest and recovery days, I ventured out and tried to see what was on offer locally - a couple well regarded Heavy Metal stores - SA Music and Revenge Records - and finally visited the Super Potato in Osaka. They had a lot of great stock obviously, but it was all heavily overpriced so it remained a visit and nothing more.
I took my son up to Americamura and Silver Ball Planet to play some pinnies off the back of the recommendation here and I was not disappointed. Many classics, a handful of old solid-states, all the way up to current-gen; Jaws, Leatherface, The Evil Dead and Halloween, etc. They also had a rare, mini Super Mario Bros Mushroom World pinball with the awesome warp pipe feature at each flipper. I've wanted to play one for years and I imagine there's only a handful left in the wild so that was a real pleasure.
The local Taito station had a nice triple stack of Egret 3's all playing various shmups which was cool to see set up. Being able to play them at midnight with only one other guy playing a mahjong game was also an experience I will remember and value.
Towards the end we went to Nara (yes, thanks again for the suggestion
@LoneSage) - the kids loved it and we got many photos, Sakura was also blooming there too which was a bonus.
Food, I ate heaps of Ramen, curry, some Udon and heaps of Konbini and McDonald's because that's mainly what the kids ate but it's fine because it's cheap and tasty.
The final day before departing was the standout, both for me and my son, we left the girls back to do some final shopping and I'd sorted two Kansai wide area passes just to venture to Kagawa Prefacture for the day, expensive, but worth it. We got the Sanyo Shinkansen and the Marine Liner, reducing a 4.5 hour trip down to 2 hours. My son was really keen on seeing a Japanese goregrind band he's been into for some time and they were playing a small gig above a restaurant with a Singapore grindcore band and a local 90's crust punk band. I'd known well in advance that they were playing and I thought it'd be cool to try and catch them and surprise my boy. We went to the gig, had some American guy there who was fluent in Japanese translate for us, but long story short, my son met one of his favourite bands, got the set list, got his CD's signed, we ended up taking many photos and met some guys that I would now consider friends. They ended posting photos and props to their instagram page which has blown my boy's mind - I've never seen him so happy.,
Oh, and I got a lead on a boxed AES unit in the region which I picked up for about USD $520. Yes, there are still deals to be found in Japan, just not in the major cities. It was a huge highlight for my trip too, knowing I'd missed my chances when I never went to Japan 20 years ago when I'd had the offer to. There was a heap of other stuff there which on the surface, was VERY good pricing - who knows if it worked or was complete but if I'd had the means and ability to have more bags at my feet containing rare consoles and video games at a metal gig, I would've. I ended up carting the box home in carry-on wrapped in jumpers and jackets to support it in the overhead compartment on the plane . Success.