Transportation from Tokyo-Osaka-Kyoto-Tokyo

Hi everyone. I'm looking for opinions on the cheapest transportation method during my 14 days in Japan.
I'll be touching down in Tokyo (NRT) around 2pm and am planning to head to Osaka right after to meet with my friend.
The rough plan is this:

30 May 2pm: Tokyo NRT
30 May (same day)-3 Jun: Leave Tokyo for Osaka
– Would a sleeper/overnight train from Tokyo be more worth the price?
3-6 Jun: Kyoto
7 Jun: Hakone (for Mt Fuji and onsen)
8-13 Jun: Tokyo

Would a JR pass or any regional pass be more worth it in the time that i'm at these places?

I'm open to any other tips and suggestions from any experienced travellers/locals.
Thanks much :)

Hello! As many people might recommend on here, the JR Pass is always the way to go but while planning my own trip, I looked into a pre-paid card called the Sucia Card as which can be used by local subways and shops within and outside of Tokyo.

You'll find more information below:

http://www.japan-guide.com/e/e2359_003.html

http://www.japan-guide.com/e/e2361.html

There might be some other options out there but this is how I will be getting around Japan. If anyone else has better options, I would like to know as well.

The Suica card is not a replacement for a JR Pass, in particular it can't be used to pay for long-distance trains such as Shinkansens.

As you have it, there are 9 days from the time you leave Tokyo for Osaka and the return from Kyoto back to the Kansai area. That means that the 7 day JR Pass which is roughly the cost of a round trip Tokyo-Osaka-Tokyo does not pay off. Neither does a 14-day pass, as the cost is too much to warrant its purchase. You can either:

1) forget about the pass and buy your tickets separately, including any night buses (there are not night trains for your trip) and the ability to use the quicker and more frequent Nozomi service,

2) shorten your stay between both places to accommodate the round trip within the 7 day period. That would mean leaving for Tokyo on the 5th on the last train out of Kyoto.

There are regional passes, but you're going to two totally different regions (Kanto and Kansai) and there is no pass for both other than the National Pass (JR Pass)

I meant "back to the Kanto area", not "Kansai".