Do we need a JR Pass?

We will travel to Japan for 11 days. We will arrive in Kansai and we will be staying in NAMBA for 7 days and 4 days in Tokyo. We're planning to visit Kyoto for 2 days, Kobe, Nara, Hiroshima then explore Osaka for 2 days before transferring to Tokyo. Do we need a JR pass? When should activate our pass? Thank you in advance!

My Detailed Itinerary

Day 1 Kansai - Namba
Day 2 Namba - Osaka - Namba
Day 3 Namba - Osaka - Namba
Day 4 Namba - Kyoto - Namba
Day 5 Namba - Kyoto - Namba
Day 6 Namba - Hiroshima - Namba
Day 7 Namba - Kobe - Nara - Namba
Day 8 Namba - Tokyo
Day 9 Tokyo - Hakone
Day 10 - Tokyo
Day 11 - Tokyo - Narita