from Tokyo to Alpine route

Hello I will come to visit Japan On 2 May 2020
Here is my tentative itinerary Plan A

D1/ 2 May : Arrive Narita – Asakusa area – Ashikaga flower park
D2/ 3 May : Tokyo city tour by Tokyo wide pass
D3/ 4 May : Tokyo – Arakura sengen Shrine - shibazakura – Mt Fuji 5th station–
Kachikachi Ropeway – Lake Kawaguchiko by Tokyo wide pass

D4 /5 May : Tokyo – Nagano – Alpine route – Toyama – stay at Takayama by JR pass
D5 /6 May : Takayama
D6 /7 May : Takayama – Kyoto by JR pass
D7 /8 May : Kyoto – Universal Studio Osaka by JR pass
D8/9 May : Osaka
D9/10 May : Leave Osaka – Airport

I plan to purchase JR regional pass for 7 days activate on 5 May and use Tokyo Wide pass for 3 days starting 2 until 4 May 2020

I have booked all the accommodation, and I’ve just find out that it’s gonna be tough to do the tours during the golden week.

Is it possible to do the above route on 5 May for Alpine Route?
Could you please advise the best way to go to Alpine Road if I stay in Takayama.
Besides JR pass, do I have to buy other tickets during my stay in Kyoto and Osaka?

Thank you so much