First timer in Japan

First time going to Japan in October and I am planning my trip and here are things I’m curious about:
– Is round trip nonstop plane tickets for around $1000 reasonable? (US to Haneda)
– How often do you guys go back to hotel to rest throughout your day?
– Should I plan attractions on weekdays or will it just be as crowded on weekends
– How long does it take for luggage transfer from Tokyo to Kyoto and from Osaka to Tokyo? Can I also transfer my luggage to my hotel earlier if it takes longer?
– I have 15 days in Japan how many days would I need in Tokyo, Kyoto, and Osaka?
– What are some foods that I must try?

Your insight is much appreciated thank you!

by jlin183

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