Golden Gai is an experience. Very small bars, some up very steep and narrow stairs and very little space. Many are for locals only (some have “no foreigner” signs), and you should ask permission to be let in - don’t be offended if you are told, quite abruptly, to go away. Typically no photography allowed. You’ll also have a minimum spend / cover charge. Many are themed. I spent a few hours in a dildo themed bar (“Foreigners allowed Tuesdays”).
The Misono building in Osaka is similar. One of the bars is like a messy students bedroom. I found a computer game one and played Mario on an original NES. For a game that's about 40 years old it still holds up well!
Actually a few people have reminded me, but when I went in August last year the exchange rate must have really been on our side, because it was ludicrously cheap. Even at Disneyland where you usually have to sell a kidney for anything, I was getting lunch for the whole family for a £15. It was ridiculous.
I've lived in Osaka for about 10 years. October can be a fantastic time but you can get unlucky with the rain. Typhoon season is September but it can still rain a lot in October - 50/50 chance. Temperature is great then though - mid twenties.
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Japan is a great place to visit for a holiday.