14-day JR pass for this scenario?

I'm looking to stay in Japan for around 12 days. So far the itinerary would look something like this:

* Tokyo Airport into Tokyo
* Tokyo to Hakone
* Hakone to Kyoto
* Kyoto to Osaka
* Osaka to Osaka Airport

I'm inclined to think that since I wouldn't be leaving from Tokyo again, the 14-day Japan Rail pass won't be worth my money. On the contrary, if I were to head back up to a Tokyo Airport, then it would be well worth my money. Is this a correct assumption?

Usually a seven day pass is not worth it if one starts in Tokyo, goes to Kyoto/Osaka area, and then returns to Tokyo. It usually takes an additional side trip to Hiroshima, Shirahama, Nagano, Kanazawa, or Takayama.

That is a seven day pass, and not a fourteen day pass. You are probably better off getting one of the Hakone passes, and paying for the Shinkansen Bullet train to Kyoto. You can get a Puratto Kodama Economy Plan ticket at about a 25% discount between Tokyo and Kyoto. Here is a link:

http://www.japan-guide.com/e/e2359.html

I hope this helps.

Yes, that is extremely helpful. Thank you so much!