Which rail pass to purchase

Hello all, and thanks in advance for any advice.
Traveling in Japan from Tokyo -- Nagoya -- Osaka -- Okayama -- Naoshima/ Teshima -- Kanazawa -- Takayama -- Tokyo.

Which is taking about 12 days (time spent in Tokyo at either end so don't need a pass for that time)

Doing the math and it doesn't seem like the 14-day JR Pass is worth it (Y46,390 for pass vs. Y33,420 to buy each of those tickets alone, by my calculations), but a pass does make everything more convenient so was wondering if anybody had any advice about alternatives/ the best way to make the above trip on a pass?

The JR East Pass doesn't appear to include the latter half of the trip (Takayama, etc.)

Any advice appreciated!

The 7 day JR Pass will pay off for your Tokyo - Osaka round trip.

Thank-you for your response, however I'm not sure that will be a viable option as I am not doing a Tokyo -- Osaka round trip within 7 days. I am doing a big loop over ~12 days and each 7-day section costs less than the 7-day JR pass and the total trip costs less than the 14-day JR pass.

Just wondering if there are any alternatives that any of you recommend?

Thanking you in advance.

I tried to calculate an expenses for your trip and it seems 14 days pass is saving you some money if you are going to use Shinkansen and Limited express (the fastest one)
Tokyo-Nagoya 12700
Nagoya-Osaka 8300
Osaka-Okayama 6670
Okayama-Kanazawa 13690
Kanazawa-Takayama 5590
Takayama-Tokyo 16300
Around 63000Yen!!!
Plus Narita-Tokyo and perhaps some short distance travel on JR

Thank-you Nadia - I think you're right! I only calculated the base fare, not included seat reservation, thank-you so much! :)