Itinerary -> Road trip

Hi,
I’m very excited as soon we leave for our 3rd trip to Japan.

It’s mostly out of excitement that I am posting this, but if anyone has suggestions, please don’t hesitate to share them.
We will be renting a car, due to travelling with a baby which adds quite some luggage.

Here is what we have planned:

3 nights in Tokyo: City dwelling, getting out of jet lag.

3 Nights in Nikko: search the car (Ashikaga, has snow tires) and driving to Nikko, visiting friends in Nikko and Utsunomiya. Edo Wonderland, Chuzenji, Nikko temples.

1 night in Manazuru: Long drive from Nikko, stopping at Setagaya flea market then enjoy the fishing town of Manazuru.

1 night in Kawaguchiko: Hakone (Checkpoint, Owukadani Fields), maybe Gotemba Outlet, then to Kawaguchiko

2 nights in Kiso machi: Kawaguchiko – Kiso Machi is quite a drive, maybe stopping in Jomon Muesum, Daigahara or Hokuto archeological Museum
Visiting Nara-juku, Tsumago and Magome.

2 nights in Nagoya: Maybe visiting Tsumago and Magome on the drive to Nagoya. 2 days in Ghibli Park. After the last day in Ghibli Park, driving directly to Kyoto

3 nights in Kyoto, visiting temples and Gion. Meeting a friend. Possible daytrip (one of them) to Osaka Aquarium, Hikone, Miyamachokita or Samegai post town.

2 nights in Takamatsu: long drive from Kyoto (3hrs+). Surely with stops on Awaji-shima. Visiting Takamatsu. A full day on Sadoshima (maybe car on ferry, maybe using busses on the island? Bicycle isn’t an option with the baby)

2 nights in Miyoshi: Visiting Kotohira on the way from Takamatsy. The visiting Oboke and Iya valley. I’m used to drive in snow and in mountains. But if it’s too bad, using train and busses.

2 nights in Matsuyama: Visiting Dogo area. Daytrip either to Uchiko or Uwajima. Or just relaxing in Matsuyama

1 night in Tokushima: now the way back starts. Long drive, maybe visiting Naruto, maybe just chilling in Tokushima

2 nights in Nara: Temples, Nara park, meeting a friend.

1 night in Ise: Visiting Ise, temples and Oharaimachi

1 night in Shizuoka: Toba-Irago ferry, then long drive, not planning much more than stops to watch beaches (Ikobe coast) and have lunch.

1 night Enoshima: Leaving Shizuoka early to get to see Kamakura, maybe Hase-dera. Next day in Enoshima

1 night tbdf, maybe Takao to visit Takaosan, or Kawagoe. Haven’t had the time to plan this properly. But thinking of visiting these two places. But it’s not too far to give the car back on the 29th day in Ashikaga.

3 nights in Tokyo Skytree area due to closness Ashikaga and Narita (both train rides without changing the train).

My wife has mostly plans for shopping in Tokyo, think we wont do that much sight seeing this time.

What are your thoughts. It’s some long days and some are more chill. Do you have recommodations, things that whe could/should visit on the way somewhere?