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osaka, tokyo and JR pass

We will be landing in Osaka on April 3 and will be our home base for 5 days travelling around the Chugoku and Kansai region. Will be visiting Hiroshima, Kyoto, Nara and probably Nagoya.
Then will be travelling to Tokyo on April 8 (with bullet train). Like Osaka, we will be using Tokyo as our home base for 8 days. Will be staying within the Shinjuku district.
Will maximise all activities around the Yamanote line. Maybe spend around 3 or 4 days for this.
Will also see Mt Fuji, the Kanto and Chubu region and if time permits the Tohoku region.
Will be leaving Tokyo on April 16.
All travellers (10 people) are nearly or past their 60’s. We are doing this trip on our own so that we can experience a personal Japanese culture.
1) Is it worth it to get a JR pass for this itinerary or any other alternative?
2) Is a hop on, hop off bus recommended?
3) What is the best time/advice to avoid the rush hour?
4) Any festival during our stay in Osaka and Tokyo?
5) April 9 is Palm Sunday and April 14 is Good Friday, which Roman Catholic Church in Tokyo says mass in English? Websites?
6) Which places in the Chubu and Tohoku region best for a half day visit with the JR pass and what regional food would be suggested?
Any advice and suggestions would be greatly appreciated.

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