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Okubo Elementary's Secret?
the mythical creature thing sounds like a taketombo or kappa story kids pass down, not actual equipment. but if u want a playground that'll actually blow his mind, hit the one in shinjuku gyoen, its huge & theres a real view of the skyline
okubo is actually in shinjuku, not the tokyo everyone pictures, and the school sits right by okubo-dori where all the korean spots are. honestly the playgrounds in that area are mostly standard issue, the big climbable stuff tends to live in the public koen not on school grounds. if u wanna impress the kid just walk him to shinjuku chuo park, theyve got way more to climb & its open to anyone. schoolyards here are locked outside hours anyway so a "secret" frame wouldnt be reachable
schoolyards in japan are usually off limits unless ur a student so that frame aint happening, kids just make up stories tbh
Sidecar bar Tokyo scam or normal?
2000 is steep for a seat charge but ginza tiny bars do run 1000 to 1500 as otoshi or table charge, so its not crazy. the part that matters is whether he told u before u ordered and whether its written somewhere. good spots usually have a little sign or menu note. walking away was fine tbh, plenty of other bars in that area without the upfront fee