Hi, planning a boys trip to japan late November (17 Nov – 2 Dec) and hoping to get some advice
First time outside home country so a bit excited and a lot of FOMO

Please check out the itinerary below and let me know if it looks good, any and all advice is welcome
Still conflicted over a lot of things so need opinions

This is still a draft, want to get an idea if the activities planned are feasible or too rushed/relaxed.
Kind of need to pack as much as possible but at the same time not get burnt out.

Itinerary below, please critique –
Nov 17 (Day1) – Hotel is in Asakusa, Senso-ji, Sumida river, Ueno Park, Harajuku, Akihabara, Asakusa hoppy street

Nov 18 (Day2) – Imperial Palace, Meiji Jingu, Yoyogi Park, Shibuya Sky, Crossing, Around Shibuya, Shinjuku, Kabukicho, Yokocho alley, Golden Gai

Nov 19 (Day3) – Kamakura, Tsurugaoka Hachimangu, Kotoku-in, Komachi Dori, Hase Dera, Slam Dunk crossing, Afternoon around Yuigahama beach, Yokohama on the way back, Minato Mirai, Chinatown

Nov 20 (Day4) – Fuji day, Kawaguchiko, Chureito Pagoda, Fuji Ropeway, Oishi Park, Onsen around there, Evening Shinjuku or Shibuya

Nov 21 (Day5) – Hakone day trip, Hakone Ropeway, Lake Ashi, Onsen, Evening somewhere Tokyo

Nov 22 (Day6) – Kanazawa, Kenrokuen garden, Omicho market, Nagamachi, Kanazawa Castle, Oyama Shrine

Nov 23 (Day7) – Shirakawago day trip, Evening leave to Kyoto mostly

Nov 24 (Day8) – Kyoto, Kiyomizudera, Ninenzaka/Sannenzaka, Hokanji, Kodaiji, Yasaka, Pontocho Alley

Nov 25 (Day9) – Fushimi Inari, Ginkakuji, Philosophers path, Nanzenji, Nishiki Market, Nishiki Tenmangu, Nijo Castle

Nov 26 (Day10) – Arashiyama, Tenryuji, Togetsukyo bridge, Monkey park, Kinkaku ji, Ryoan ji

Nov 27 (Day11) – Osaka Castle, Nishinomaru Garden, Osaka Museum, Shitennoji, Keitakuen garden, Dotonbori, Shinsekai

Nov 28 (Day12) – Katsuoji Temple, Minoo Falls, Umeda Sky Building, Hozenji Yokocho, Namba Yasaka, Dotonbori

Nov 29 (Day13) – Nara Day, Kofukuji, Todaiji, Nara Park, Kasuga Taisha, Harushika Brewery, Naramachi

Nov 30 (Day14) – Flex Day for either Kobe / Koyasan Day trip or Tokyo Return for revisits

Dec 1 (Day15) – Teamlabs Planets/Ghibli Museum, Ginza, Roppongi, Souvenir shopping

Dec 2 (Day16) – Departure

Few questions

1. Can Osaka can be compacted more ? For other day trips or a different city.
2. As for Hakone, is it worth if I already have a Fuji day at Kawaguchiko? Would Nikko be a better daytrip?
3. Suggestions for the flex day and any other locations that i should include and am missing out on
4. Is the route good or has room for optimization, I was thinking to add kanazawa at the end after Osaka.

Also where can I get good deals on hotels, what are budget friendly options, booked APA in Asakusa for Tokyo as of now.
Food and other suggestions are also welcome

Thanks!!!