Obon & reservations

I am traveling to Japan to arrive in Tokyo Tue 12th Aug 2025.
I understand that even if I book the Japan rail pass today to get delivered to my Guest House in Tokyo, I may not receive it by Tue the 12th when I arrive (since it is already Sunday 10th Aug 2025).
The hope is to travel from Tokyo to Kyoto on 14th Aug 2025, just before the Obon festival.
If I get the JR pass, will it be too late to try to reserve seats on the 12th or 13th of Aug for next day travel ?
Also from Kyoto to Nara on 15th Aug 2025. I am worried that it will be a peak travel day and the JR line may be very full and we will be unable to get a reservation.
Similarly to return to Kyoto in the night fof the 15th.

We are also wondering what the crowds will be like in Kyoto for the weekend and whether we will have any chance of seeing the monkeys at Iwatayama Monkey Park in Kyoto on Sunday 17th Aug 2025 or whether it will be so packed with tourists that we may not have a chance.

Last, we want to take the train from Kyoto to Ichinoseki on 18th Aug 2025. Again, wondering if the Obon crowd will make this difficult or impossible to reserve seats and whether it makes more sense to try to buy them without the JR pass online today.

I realize that there is a 24hr delay before my question is posted to avoid spam and another 24 hour delay before my question is answered, so perhaps my planning is too late but I thought I should try anyway to ask.

Thank you in advance,
Anjana.