Tokyo-Nikko-Tokyo
Tokyo-Kawaguchiko (looks like a bus may be a better choice here)
Kawaguchiko-Kyoto (bus?)
Kyoto-Osaka
Osaka-Kobe
Kobe-Himeji
Himeji-Hiroshima
Hiroshima-Miyajima-Hiroshima
Hiroshima-Tokyo

http://www.japanrailpass.net/eng/en009.html

To turn in your Exchange Order for your JR Pass, you have to set the date of activation. You can not change the date after getting your JR Pass.
If you have decided the date of activation by the time you reach your station (of JR-East) in Narita Airport, then you can get your JR Pass there.
http://www.japanrailpass.net/eng/en006.html

: i'm wondering if the 14 day JR pass would be worth

The price of a 14-day Ordinary JR Pass (for an adult) is 45,100 yen.
When you choose non-JR for your Nikko round trip and a highway bus to get to Kawaguchiko area....
- The regular JR cost # surpasses 45,100 yen
if you take Shinkansen and other Ltd. Express trains as many times as possible,
even for shorter-distance sections.
- You can hold down the JR cost # to 42,200 yen or less with no rides Shinkansen NOZOMI,
if you head to Kyoto Station and come back to Tokyo Station within 12 days on dates;
under this condition, the JR cost # does not surpass 45,100 yen
even if you have Shinkansen NOZOMI rides, which are not covered by JR Passes,
for Tokyo - Kyoto, Hiroshima - Himeji and Hiroshima - Tokyo.
# The regular JR cost from the Day 4 until reaching Narita Airport.

Your options include taking Tobu Railway lines between Asakusa and Tobu Nikko stations.
- If you lodge near a Yamanote Line station of JR-East,
then you can get to Asakusa Station of Tobu with no or one transfer.
- The Tobu cost (= 2 x 2,620 yen) including Ltd. Express charges is about the same
as the JR cost not including Shinkansen charges between Tokyo and Nikko stations.
- If you plan to lodge in Nikko, then Tobu passes sound worth considering,
though they don't cover Ltd. Express charges (= 2 x 1,300 yen).
http://www.tobu.co.jp/foreign/pass/index.html

: Kobe-Himeji

If you plan to visit Himeji Castle in coming November 2009, then make sure that renovation works on its Main Keep will begin in coming October.
- According to the renovation schedule, you can see its Main Keep from inside the castle in November 2009.

: Tokyo-Kawaguchiko (looks like a bus may be a better choice here)

Yes. Daytime highway buses are available from a highway bus terminal near West Entrance of JR-East Shinjuku Station.
(1,700 yen: Highway bus: One way: Shinjuku Sta. Bus Terminal - Kawaguchiko Sta. Bus Stop.)
http://www.japan-guide.com/e/e6905.html

: Kawaguchiko-Kyoto (bus?)

I don't recommend your taking an overnight highway bus for this leg,
considering that you plan to visit many places in western Japan after it.
Various railroad routes are possible. The following one seems to be simple, though you will have a bit long walk in Tokyo Station.
Kawaguchiko --[Fujikyu]-- Otsuki --[JR-East]-- Tokyo --[JR-Central: Tokaido Shinkansen]-- Kyoto.
(1,110 yen: Fujikyu fare: One way: Kawaguchiko - Otsuki.)