Osaka-Kobe-Kyoto-Tokyo

Hi there,

seeking for your opinion for my trip, from osaka to tokyo, below are my plan (total 9 days at Japan)
1. 16 - 19th Oct (Osaka) - KIX airport
2. 19 - 21th Oct (Kobe)
3. 21 - 23th Oct (Kyoto)
4. 23 - 24th Oct (Tokyo) - Haneda airport

Do I really need to purchase JR Pass? If yes, when can I start using it? Because not worth if purchase 14 days JR Pass.

Thanks.

warm regards,
Toby