Any suggestions for the 15 days itinerary

We are planning our first trip to Japan in mid-Nov (19.11-04.12). We fly to Tokyo and return from Tokyo Narita. 15 days.
Our preliminary plan looks like this:

Tokio-Osaka (sleep)
Osaka- Koyosan (sleep)
Koyosan- Kyoto (sleep)
Kyoto - 5 full days, with day trip to NARA and Yamazaki
Kyoto-Kanazawa (sleep)
Kanazawa-Shirakawago-Takayama (sleep)
Takayama- Matsumoto- Nagano (sleep) or straight to Tokyo (if possible)
Tokio - 5 full days

-If this idea straight from Narita to Osaka (sleep) and then to Koyosan (sleep) make sense? Or better to do the Koyosan after 5 days in Kyoto?
-Just wondering, if it is not to rush the Kanazawa & Takayama days?Will that plan give me enough time to explore most of the places? Or should I stay an extra night in Takayama or Kanzawa?
-Is this region good for trying the Ryokan expierience ? Or No idea if make sense to better to change the itinerery and add extra night in Hakone (on the way to Tokyo)?
-Is it better to add a Himeji castle as a day trip from Kyoto and drop the Matsumoto castle? Then go straight from Takayama to Tokyo? Or Takayama- Matsumoto and sleep in Nagano seems to be not to tired? Or would it make sense to do Takayama- Matsumoto-Tokyo?

-Not sure when to activate the Rail Pass?

Sorry about all the questions and thank you for your help in advance.

Thank you in advance for all the help!

Overall it's a good itinerary, I think. What time will you leave Kyoto for Kanazawa? If you leave Kyoto late in the day you may want to take one more night to enjoy Kanazawa. I have never been to Matsumoto castle, but Himeji is quite spectacular; I think it would be worth a day trip.

A big part of your route won't be covered by the JR pass so I don't know if the pass will be worth it for you.

Out of the places you have chosen, Takayama (or some places nearby like Hida) would give you some great ryokan options; there is no need to go to Hakone just for a ryokan. You could also find ryokan in the Kyoto area or Kanazawa.

Thanks Gigi!

I've checked and the JR Pass and it won't work for us. In the frist version. We've changed out intinerary a little and decided to skip an overnight in Takayama. Maybe now it will work out?
If not then we will have to stick to the local trains and different connections and that would be quite challenging , I belive.

Do you think is doible to do the Shirakawago & Takayama from Kanazawa within one day and go back to Kanazawa for overnight? As per below:

Tokio-Osaka (sleep)
Osaka- Koyosan (sleep)
Koyosan- Kyoto (sleep)
Kyoto - 5 full days, with day trip to NARA and Yamazaki distillery
Kyoto-Kanazawa (sleep)
Kanazawa-Shirakawago--Takayama-Kanazawa (sleep)
Takayama- Tokyo
Tokio - 4 full days

I was told also to consider flying to Osaka (instead of train), to save some time and money (cheap flight). Do you think it's a good idea? Our arrival is at. 9;00 am and the flight to Osaka is at 11:30 am. Will we managed to catch the flight (taking into account to get the temporary visa etc.)?

Thank you.

Could you please help me with the "middle" part of my initerary?

From 21.11 (late evening) until 27.11 (morning) I will be in Kyoto (so 5 full days ). Then I will be on the 29.11 (late evening) until 04.12 (deparature) in Tokyo (4 full days).

I still have not a plan for the time between Kyoto and Tokyo, on the 27-29.11 (2 nights). Have you any suggestions? I would be grateful.

I am considering any place in Alps, maybe? Or near Nagano (maybe some onsen place with the view?) or a place near Fuji?
I will probably not have JR Pass.

Thank you in advance.