5D5N itinerary in September

Hi,

I will be arriving in Haneda airport on the morning of Sep 10th around 7am.

The following are what I am thinking for my itinerary:
10th: Ginza then off to Matsumoto. Stay at Matsumoto. I have a small errand to run for a friend near the Ginza area before I can start my trip.
11th: Tateyama Kurobe Alpine Route. Stay at Toyama
12th: Kurobe Gorge/Toyama. Stay at Takayama
13th: Half day tour to Shiragawa-go village and Takayama. Stay at Nagoya
14th: Nagoya and maybe Osaka. Stay at near Kansei airport or spend a night at the airport
15th: flying out from Kansei airport at 8:00am

1. Will this be too rush and not enough time at each place?

2. Is there have any discount ticket for my itinerary I can use other then JR rail pass? I know that the Tatayama Kurobe Alpine Route and the Kurobe Gorge are not covered by the JR pass for sure, but I am not sure about the other. I am also thinking about taking bus from Takayama to Nagoya and Nagoya to Osaka to save me some money.

Any suggestion are welcome. Thanks in advance for your help.

It is not too rush. But it depends on the person.
For me I would like to spend more time in each place. Especailly Takayama
Stay a night at Takayama or Shirakawago
Nagoya is lovely but you should skip it if you are only in Japan for 5 days.
After Takayama/Shirakawago, you can go to Kanazawa.
2 hours for the garden, 1 hour for the castle, 3 hours for the samurai+Geisha+merchant districts.
Maybe even stay in a onsen hotel. The region has many onsen towns.

Take the direct limited express train to Kyoto the next day
Spend some time in Kyoto
Take the train to Osaka and sleep there. If you take the 4:58 am train you would reach the airpot by 6:30am

Thanks Joshua for your suggestion. I did do some research on Kanazawa. I have been to Kyoto before. To me, Kanazawa is kind of like Kyoto, that's why I decided not to go there. I will do some more research on Takayama and surrounding before I finalized my trip.

Ah, the reason I recommended Kanzawa is because
1. It has a beautiful garden
2. The castle grounds are large but I don't like castles so don't ask me whether it is nice
3. The food here is really top notch. It is smacked between many farming areas. And it itself is a city. So you have cheap ingredients cooked by good chefs. Wagyu beef from 3500 yen upwards. Sirloin from 2500 upwards
4. There are onsen nearby

If you do go to Osaka, try to stay near Namba or Tennoji