Feedback on Itinarary September 18

Hello, my spouse and I (both in our early 20's) will be traveling this September to Japan to for a 4 weeks travel.

We have constructed the following plan: https://m.imgur.com/a/gQaiQv7

I would be happy to receive some feedback:
- Allocated time in each place.
- Uses for Jr pass ( I understand that some advise to place kyoto before Hiroshima to better use the pass, but these dates are fixed for us).
- Between kyoto and Hakone, is the itinerary ideal regarding the transportation between them?
- Sleeping in Nagoya, is it a good idea just as a stop by on the way to hakone? Or should we consider some place else in between?

Another question we have been struggling to find an answer to, is about the luggage delivery.
Is there a website where I can easily find if a hotel is working with a takkyubin? In case we would like the luggage to be sent to our Tokyo hotel, so that the alps travel would be light - is it possible to post luggage a week in advance?

Thanks in advance!

There should be so many options to complete your itinerary, so I will write just one option.

Buy Kansai Hiroshima Area Pass (13,500) and use it for 09/09 to 13/09.
https://www.westjr.co.jp/global/en/ticket/pass/kansai_hiroshima/

To go to Tokushima, the fastest way is to take highway bus which is of course not included in the pass.

http://www.jr-shikoku.co.jp/bus/global/en/route/awa_ex_osaka.html

Reservation
https://www.kousokubus.net/JpnBus/en

To go to Kanazawa from Kyoto, buy normal ticket (6,900 yen for non-reserved seat).

From Kanazawa, buy Mitsuboshi Route Shinjuku ticket.

https://www.bus-navi.com/news/d3537db208ce9dcd2aff.pdf

You can go to Shirakawago, Takayama, Hirayu onsen (transfer to Kamikochi, additional 2,050 yen round trip), Matsumoto and then Shinjuku (in Tokyo). The validity period is 7 consecutive days.

So the total cost is: 3,700 (bus to Tokushima from Osaka) + 2,640 (JR limited express non reserved seat from Tokushima to Takamatsu) + 13,500 + 6,900 + 8,560 = 32,660 yen.

With this option you will have some flexibility for the traveling time. For example you can stay longer in Kyoto without worrying about the validity period of Japan rail pass. In addition this would be cheaper than 14 days JR pass plus some bus ticket.

Other comments.

Try to avoid Saturdays on busy place such as Kyoto, Osaka and Kyoto.

Why do you include Tokushima? Personally, I think Himeji, Okayama, Takamatsu are more interesting. If you omit Tokushima you will save some money.

Your itinerary it too gTokyo-orientedh. Try to allocate less for Tokyo and more for Kyoto, some smaller cities (Kanazawa and Matsumoto for example) and rural areas such as Kamikochi.

Is there a website where I can easily find if a hotel is working with a takkyubin?

As far as I know there is no such website. But at the same time I can't imagine of a hotel which does not receive/send Takkyubin. Takkyubin is so deeply accepted by Japanese life so we don't mind about that.

In case we would like the luggage to be sent to our Tokyo hotel, so that the alps travel would be light - is it possible to post luggage a week in advance?

http://www.kuronekoyamato.co.jp/ytc/en/contact/qa/01.html

We accept requests for delivery on your desired delivery date. (No additional fee.)

You can select the delivery date to be a date up to one week after you send the parcel.
Please inform us about the date when you apply for delivery.