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Solo advice for Tokyo and Hong Kong

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Hey guys - I just booked a trip to visit the neon metropolises of Tokyo and Hong Kong for September. I'm 30/m . I have never been to either place before and thought since I was travelling solo that a hostel would be preferable to a hotel or airbnb. I had a few questions for everyone:

- can anyone recommend a good hostel in a good area, somewhere were I can mingle with other travellers, have a drink at night with. Not looking to spend more than $100USD/night

- clothing - do you need pants or shorts in September? Rain jacket?

- how much cash (yen/HKD) should you bring (5 days in each city)

Any other advice?

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