Can I active the 7 Days JR PASS on Day 3-4?

Hello, please help to check below itinerary, I have checked the site that 7 Days JR PASS is better than 14 Days JR PASS, but I don't know can I active the pass on the Day 3 to Kobe or Day 4 to Nara in Osaka station. Because the long distance trip to Tokyo in on the Day 5, so if active it on arrival to KIX, it will be expired before I come back to Kyoto. Please advice.

Below itinerary is a rough plan, basically, I will stay in each city for 2-5 days. If JR pass is not worth it, can I just use my ICOCA to travel between KIX - Osaka - Tokyo - Kyoto - KIX

DAY 01 Kansai International Airport - Osaka (Namba)
DAY 02 Sightseeing in Osaka
DAY 03 Osaka - Kobe - Osaka
DAY 04 Osaka - Nara - Osaka
DAY 05 Osaka - Tokyo
DAY 06 Sightseeing in Tokyo
DAY 07 Sightseeing in Tokyo
DAY 08 Tokyo - Kamakura - Tokyo
DAY 09 Tokyo - Kyoto
DAY 10 Kyoto- Uji - Kyoto
DAY 11 Sightseeing in Kyoto
DAY 12 Sightseeing in Kyoto
DAY 13 Sightseeing in Kyoto
DAY 14 Sightseeing in Kyoto
DAY 15 Sightseeing in Kyoto
DAY 16 Sightseeing in Kyoto
DAY 17 Kyoto - Kansai International Airport