JR Pass and Yamanote line

Hello! Would you recommend purchasing a JR Pass based on my itinerary in January?

Jan 1-2: Osaka
3: Osaka - Kyoto - Osaka (day trip)
4: Osaka - Hakone
5: Hakone - Tokyo
6-7: Tokyo
8: Haneda Airport

Second question, if I do purchase how would I use the JR Pass to travel the Yamanote Line in Tokyo? Do I physically show it to ticket guard or can I link the JR Pass to an IC card to use the automated gates? Thanks