Overwhelmed First-Timer

Hello everyone, I plan on visiting Japan for two weeks in early March 2023. I’m in the process of working on my itinerary and although I have a general idea as to what I want to do, I overthink and tend to stress myself out so I’d like y’all’s input, please. My flights are already paid for: less than $300 from my city to LA then $725 from LA to Tokyo. I’m working on my itinerary as far as what all I plan on doing each day but here is a general idea:

•February 28: Flight to Tokyo

•March 1-6: Tokyo

•March 5: DAY TRIP-Hakone

•March 6-9: Kyoto

•March 10-14: Osaka

•March 13:  DAY TRIP-Nara

•March 14-15: Tokyo

I also have my hotels booked:

•March 1-6: Hotel Metropolitan Tokyo Ikebukuro $323.38

•March 6-9: Matsubaya Ryokan $165.96

•March 10-14: Willows Hotel Osaka Shinimamiya $229.68

(Still need to book final hotel for last night in Tokyo)

I don’t plan on doing a lot of shopping; I predominantly travel to explore, eat and learn more about the culture. That being said, I do love food; a lot, and would say that’s where most of my money will go.

My questions are:

1. Do you think it’s a good idea for a first-timer to venture out of Tokyo? Any suggestions as far as what all to see and do? I really don’t want to get too deep into planning yet, just in case I have to start over but a few places I’m pretty certain about are:

•Ghibli Museum
•Harajuku
•TeamLab Planets
•Shibuya Sky
•Akihabara
•Kobe(?)
•Seven Waterfalls (Izu)
•Nara Park
•Osaka Castle
•Mt. Fuji
•Fushimi Inari Taisha
•Arashiyama Bamboo Grove
•Joël Robuchon Restaurant OR a really good restaurant to get A5 since I’ll be in Japan (open to suggestions)

2. Should I get the JR Pass? I’ve read arguments for and against getting it.

3. How much spending money do you think I should bring with me? I’ll probably get some souvenirs for 3 people. Yes, I enjoy anime and manga but not enough to spend a ton of money buying merch for myself.