Cheapest Rail Pass (or No Pass at All?)

So we don't know what the cheapest option is going to be. We're considering the Seishun 18 Kippu, but it seems like it may not pay off. Perhaps the Hokkaido and East JR Pass?

We'll be traveling in the Tokyo area from Aug. 27 (arrival date) to Aug. 30, when we want to take some sort of overnight transportation in order to arrive in Hikone on the 31st.

Aug 27:
Train from airport to hotel (Minami-senju)

Aug 28:
Ginza and Tsukiji
Yokohama

Aug 29:
Mitaka
Shibuya
Roppongi

Aug 30:
Higashi-Ikebukuro
Random travel in the city
Overnight train to Hikone/Kyoto?

So we're trying to find the cheapest pass for this. I'm beginning to think the 18 Kippu won't pay off, but it makes riding the Moonlight Nagara easier. I don't understand how to reserve tickets for that without the Kippu. Would the Hokkaido JR East be better for this trip? Is there another option besides those?

Are you making the return trip to Tokyo? If you post your whole itinerary, we can give better advice...

There is no Hokkaido JR East. JR Hokkaido pass is for Hokkaido and JR East is for East Honshu.

If you leave out of Osaka, there will be no pass that will pay off. Just use and IC card and Nozomi to get to Kyoto.

Let me clarify: You will head to visit Hikone City in Shiga Prefecture known for a castle, not Hakone Town in Kanagawa Prefecture known for a view of Mt. Fuji. Is that right?

Westbound Moonlight Nagara (extra Rapid trains) will not be available on August 24 or later in this summer.

Seishun 18 Kippu does not allow you to take any JR Shinkansen or Ltd. Express train from Tokyo to Kyoto, so it demands you to make a much more time-consuming and complicated trip. It cannot be recommendable except to railroad fans.

- Hikone: Access and Orientation
http://www.japan-guide.com/e/e7003.html
- Kyoto: Access and Transportation
http://www.japan-guide.com/e/e2363.html

NOT: You will head to visit
BUT: You will head to

To Hakone Town you can make a daytrip from Tokyo or, if you leave Tokyo in the morning, make a side trip on your way to Hikone City / Kyoto City. (Areas around Mt. Fuji may be crowded with family visitors in the last weekend of August, though.)

Thanks everyone for the tips!

@scareddragon This IS my whole itinerary. This is not an exclusively tourist trip. I am just showing friends around before moving in in Hikone, so I will not be returning to Tokyo.

@omotenashi I am indeed going to HIkone, in Shiga prefecture, where I will be living for a while. It seems that my best option for cheap travel at this point might be a night bus. Would you agree? Since it seems that overnight trains going westbound will not be available. I can make the same trip on around 7300 yen if I don't take expensive trains (express, shinkansen, etc), but add another 3700 for a night at a hotel and it looks like an overnight bus might be a good option, yes? Are there alternatives to an overnight bus?

I appreciate everyone's help!

If you wanna travel overnight then night bus is your best option. JR Nishinihon operates night buses between Ikebukuro and Hikone Stations. They cost around 7500 yen. You can find other buses on this route as low as 5000 yen.

http://www.kakuyasubus.jp/search/detail/10932/0806/35301/35061

Thanks for that link! It's in Japanese, but that's fine. I can read it, so I found a route from Ikebukuro to Hikone, as you mentioned.

Two things I'm unsure of, though. First of all, I don't really know what the symbols mean. Do these buses have toilets (or say how often they make stops)? Also, when I tested out the process, it said the business was closed for the day. That leads me to believe that you can't book these buses ahead of time. Is that true?