Need help with 2 weeks itinerary.

Hey all, I posted 2 threads in this forum and everyone was really helpful. I'm planning to visit Japan alone in June for about 2 weeks. I've just finished my brief itinerary. This is obviously not the best so I�fm going to need your help here. Any opinion would be highly appreciated.

Tokyo
June 6th (Friday): Fly from Bangkok to Narita Airport. Arrive in the morning. Planning on going to Naritasan and then to Ryokan Toukaisou.
June 7th (Saturday): Senjoji Temple and Kappabashi Street in the morning. Tokyo Imperial Palace and Akihabara electronic in the afternoon. Then Roppongi at night.
June 8th (Sunday): Meiji Shrine, Ebisu and Harajuku all day. Visit Shibuya in the evening if time permits.
June 9th (Monday): Tsukiji Market early morning and Sony Building later. Then visit Shinjuku in the afternoon.
June 10th (Tuesday): Rikugien Garden and Ueno Park
June 11th (Wednesday): Kamakura in the morning and Yokohama (ramen museum) in the afternoon.
June 12th (Thursday): Hakone
June 13th (Friday): Spend one full day in Tokyo.

Kansai
June 14th (Saturday): Leave for Kyoto. Visit Kiyomizudera Temple.
June 15th (Sunday): Kinkakuji Temple and Daitokuji Temple in the morning. Visit Kuruma in the afternoon.
June 16th (Monday): Visit Katsura Rikyu and Tenruji Temple in Arashiyama. Take it easy in downtown Kyoto in the late afternoon.
June 17th (Tuesday): Visit Fushimi Inari Shrine in Southern Kyoto. Leave for Nara in the afternoon. Check in at Ryokan Matsumae.
June 18th (Wednesday): Visit Nara-koen area.
June 19th (Thursday): Leave for Osaka. Check in at Osaka Shiritsu Nagai Youth Hostel. Visit Osaka and take it easy in the evening.
June 20th: Fly from Osaka back to Thailand.

I'm really new here so I'm going to have many questions:

Is Naritasan worth the trip especially after the night flight?

How long do I need for Hakone? Am I better off going to Kusatsu?

Is my Kansai schedule enough to get a good feel of Kyoto and Nara? Or am I better off just staying in Kanto for 2 weeks?

Would the JR pass worth my trip? If so, shall I buy 1 or 2 weeks?

Do you have any thoughts on Toukaisou Ryokan in Asakusa?

How bad would the rain affect my trip?

Temples, shrines, and nature are the main area of my interests. If I go to places like Nikko, would that be enough to cancel the trip to Kansai region?

Again, I�fm really sorry with excessive questions but this would be my first time that I�fll be sightseeing in Japan (I�fve been there many times but for tennis tournaments). Thank you so much for your opinion.

is Naritasan worth the trip especially after the night flight? it is an interesting temple but you will see many interesting temples so skip it.
If I go to places like Nikko, would that be enough to cancel the trip to Kansai region? absolutely and definitely not! the Kansai has many more sights than Nikko, Kamakura etc. If anything you should spend more time in the Kansai than in Tokyo. Most of the "famous" neighbourhods in Tokyo can all be seen in 2-3 days as they are somewhat similar (a JR rail station, office buildings, big department stores, other stores, bars, restaurants). Osaka has neighbourhoods just as interesting and lively.
sorry about not being able to answer the other questions.

Is Naritasan worth the trip especially after the night flight?
After an overnight flight, I think it would be easier for you if you traveled directly to Tokyo and make yourself comfortable at the hotel :)

How long do I need for Hakone? Am I better off going to Kusatsu?
If you want the "onsen" hot spring experience, you might want to stay overnight. If not, I believe you can do the round-trip in a day from Tokyo.

Is my Kansai schedule enough to get a good feel of Kyoto and Nara? Or am I better off just staying in Kanto for 2 weeks?
Definitely splitting your time between Kansai and Kanto, like your schedule, is good.

Would the JR pass worth my trip? If so, shall I buy 1 or 2 weeks?
JR Pass makes sense only if you make long-distance trips within a relatively short period of time - for example, a 7-day Japan Rail Pass is worth IF you make a round-trip between Tokyo and Kyoto/Osaka within that 7-day period on Shinkansen superexpress trains. Or if you go as far as Hiroshima and return, yes. But since you are only going one-way, and except for the Tokyo - Kyoto segment, your trips are relatively short-distance. So I think it would be better if you buy single tickets as you go, or at most use SUICA prepaid card for Tokyo.

How bad would the rain affect my trip?
Weather - it's really a matter of luck. And many places like Kyoto and Nikko are beautiful on rainy days too.

Temples, shrines, and nature are the main area of my interests. If I go to places like Nikko, would that be enough to cancel the trip to Kansai region?
Please definitely go to Kansai as well.

Red Frog and AK, Thank you so much for your opinion. I would then definitely go to Kansai. I might just stay in Kyoto and visit Nara as a day trip instead of having to move there. Do you recommend any decent budget ryokan?