Guidance needed with 18 day itinerary rework

Hello again to all the great advisors here in this forum.
Just now beginning to wonder about switching up this itinerary entirely based on the fact that this is my second solo Japan trip and I have a basic idea of what I’m most interested in.
That being said what would anyone here in the forum change about the following stops/nights spent and route that I’ve come up with so far.

Tokyo 11/2-11/4 (3 nights)

Matsumoto 11/5 (1 night)

Tateyama Kurobe Alpine Route 11/6 (1 night in Tateyama)

Takayama 11/7-11/8 (2 nights)

Shirakawa-go 11/9 (1 night)

Kanazawa 11/10-11/11 (2 nights)

Kyoto 11/12-11/16 (5 nights)

Osaka day/nite trip from Kyoto*
Nara day trip from Kyoto?

Tokyo 11/17-11/19 (3 nights-6 nights total in Tokyo)

Lake Kawaguchi and Lake Sai at Fuji five lakes day trip from Tokyo*
Kamakura side trip from Tokyo*?

Wondering which of the two experiences between the Tateyama Kurobe Alpine Route and the Magome-Tsumago Kiso Valley hike would be possible or could I do both? Being as I live in NYC I’d like to experience both epic nature with as much Koyo viewing as possible in the afforementined places during the first three weeks of November,
as well as smaller places with lots of character.
I don’t mind spending a night or two in a quiet place with no activity as long as there’s some vibe and access to something to eat.
What would be the best possible way to route one or both of these trips in addition to the 5-6 nights in Tokyo, 4-5 nights in Kyoto and 2 nights in Takayama out of 18 days/nights in total?
Also is Matsumoto really just a jumping off point for either of these trips and a few hours stop for the Castle etc. and you wouldn’t want to stay there overnight? Same is Kanazawa better for 1 or 2 nights and is Shirakawa-go a nice place to spend a night? Or forego Shirakawa and Kanazawa entirely for the Alpine Route and or Magome-Tsumago Kiso Valley considering I’m going to want a nice balance from Tokyo and Kyoto?

Lake Kawaguchi and Lake Sai at Fuji five lakes day trip from Tokyo*
Kamakura side trip from Tokyo*?

Save them for your last 3 days in Tokyo then. At that point, after seeing the JAlps and temples of Nara and Kyoto, you can decide if you want more but lessor forms of the same or if you want to explore the wonders of Tokyo more.

Wondering which of the two experiences between the Tateyama Kurobe Alpine Route and the Magome-Tsumago Kiso Valley hike would be possible or could I do both? Being as I live in NYC I’d like to experience both epic nature with as much Koyo viewing as possible in the afforementined places during the first three weeks of November,
as well as smaller places with lots of character.

They are very different. The Alpine route is longer, with more spectacular mountain views while the Kiso valley has more history and culture.

I don’t mind spending a night or two in a quiet place with no activity as long as there’s some vibe and access to something to eat.
What would be the best possible way to route one or both of these trips in addition to the 5-6 nights in Tokyo, 4-5 nights in Kyoto and 2 nights in Takayama out of 18 days/nights in total?

Kiso Valley is an easy day trip from Matsumoto, or easy from between Nagoya and Matsumoto.

The Alpine route can be done from either Matsumoto or Takayama, although it's probably better from Toyama or Kanazawa.

Also is Matsumoto really just a jumping off point for either of these trips and a few hours stop for the Castle etc. and you wouldn’t want to stay there overnight?

Matsumoto is a fine town, but no it isnt a huge tourist attraction. It's just kind of ordinary outside the castle and mountains.

Same is Kanazawa better for 1 or 2 nights and is Shirakawa-go a nice place to spend a night?

Kanazawa is a really interesting place. It's much more interesting than Takayama, which you still have 2 questionable nights in.

Shirakawago is a tiny tiny village and extremely touristy. I dont advise staying the night.

Or forego Shirakawa and Kanazawa entirely for the Alpine Route and or Magome-Tsumago Kiso Valley considering I’m going to want a nice balance from Tokyo and Kyoto?

It boils down to your interests. I wouldnt skip Kanazawa, not when there is so much fat in your itinerary like Osaka and Takayama; but if it doesnt float your boat, jettison it.

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