Please check my itinerary -

Hi Ryan,

Ideally you'd use a 7 day JR Pass for travel to Takayama - Osaka - Kyoto and return to Tokyo before the pass expires.
Your itinerary is one which makes it hard to make good use of a JR Pass.

Narita Airport - Tokyo ¥ 2,940
Tokyo - Takayama ¥ 14,300
Takayama - Osaka ¥ 10,310
Osaka - Kyoto ¥ 540
Kyoto - Tokyo ¥ 13,220
Tokyo - Narita Airport ¥ 2,940

For a total of ¥ 44,250 this is just below the price of a 14 day JR Pass (¥ 45,100). A 7 day JR Pass is ¥ 28,300 however right now I don't see where you make use of it to make savings, without making changes to your schedule. I'd recommend either using a 14 day JR Pass for your complete itinerary, it is also good for local travel around Tokyo and Osaka so you'd probably still make small savings, the other advantage here is that you only have one ticket for all your travel and don't need to purchase tickets every time. Alternatively you could go for normal tickets as you travel.

Hope this helps!
Daniel