Hi Eric,
I've made a list of ticket prices to find out!
Tokyo - Takayama ¥ 14,300
Takayama - Ogimachi, traveled by bus and not included in pass.
Ogimachi - Kanazawa, traveled by bus and not included in pass.
Kanazawa - Koya (covered up the Osaka) ¥ 7,440
Osaka - Kyoto ¥ 540
Kyoto - Tokyo ¥ 13,220
For a total of ¥ 35,500. This is right between the price of a 7 day (¥ 28,300) and 14 day JR Pass (¥ 45,100). Looking at your travel dates I think that it would be best to buy normal tickets for now as you travel more than 7 day but a 14 day JR Pass would not pay off right now.
A little clarification for travel to Koya. The last part to Koya san is traveled on the Nankai Express which is not covered by the JR Pass and requires an additional fee of 850yen.
Hope this helps!
Daniel