Is my itinerary okay for first timer?

I’ll be traveling to Japan with my father (22M & 50M) from Oct 19–29. This is the itinerary i prepared took me about 3-4 days to plan this…

Oct 19,20 – Tokyo
* Senso-ji Temple and Nakamise Street
* Shibuya Sky, Shibuya Crossing, Hachiko statue, Nintendo Tokyo
* Starbucks Reserve Roastery Nakameguro, Kokyo Gaien, Akihabara, Ueno Park, Yanaka Old Town

Oct 21 – Hakone
* Tozan train, cable car, ropeway to Ōwakudani
* Lake Ashi pirate ship cruise, Hakone Shrine

Oct 22 – Kyoto
* Fushimi Inari, Kiyomizu-dera, Ninenzaka/. Sannenzaka
* Imperial Palace for Jidai Matsuri parade
* Arashiyama: Sagano Romantic Train, Hozugawa River boat ride, Bamboo Grove, Tenryu-ji, Togetsukyo Bridge

Oct 23 – Amanohashidate & Ine Funaya
* Chairlift and monorail viewpoints
* Visit Ine Funaya boat houses

Oct 24 – Osaka
* Katsuo-ji Temple, Osaka Castle, Namba Yasaka Jinja
* Explore Dotonbori

Oct 25 – Gifu
* Mt. Kinka Ropeway and Gifu Castle, Gifu Daibutsu
* Gifu Old Town

Oct 26 – Magome & Tsumago Hike

Oct 27 – Nagoya
* Nagoya Castle and Hommaru Palace
* Ghibli Park
* Osu Shopping Street, Nagoya TV Tower

Oct 28 – Nagoya → Tokyo
* Shinjuku Gyoen, Meiji Shrine

What i want to know
1. As this is my first time, is this plan realistic??
2. Should i buy the hakone pass?
3. Have I congested too many things for a day??
4. Anything I should add, remove, or replace?
please advice me…

by Levi_0_0_0_