Is a regional pass best for me?

Hi Daniel San,
My boyfriend and I plan to travel to Japan in January. We will arrive on Jan. 7 but will stay in Tokyo until Jan. 12 when we plan to go to Kyoto for 3 nights and possibly visit Nara and Osaka. From there we plan to go to Kinosaki Onsen from Jan. 15-17 and then make our way back to Tokyo. Do you suggest a regular 7-day JR pass? Or a regional Osaka-Tokyo pass?

Also, when is the best time to order the pass? Can we order it now before the price goes up in October?

Thank you for your help!
Alana