Comparing 14 days JR Rail Pass vs. buying each tickets.

14 Days JR Rail Pass: US$ 423/person

Fare calculation is based on a routing you have posted:
Tokyo – Kyoto – Osaka – Nara – Hiroshima – Tokyo

Buying each tickets:

Under your situation if you can make the trip leaving Tokyo and arrive back to Tokyo in 12 days then that will be cheapest, because you can take advantage of round trip discount on base fare (乗車券).

Best under this routing will be buy round trip ticket as:

Tokyo –(Shinkansen)- Kyoto – (local commuter train)- Osaka –(Shinkansen)- Hiroshima – (Shinkansen)- Tokyo

To the above buy separate round trip ticket of Osaka – Nara on local commuter train.

Total of above using Nozomi will come out to 39,928 yen/person, or US$ 388.74/person.

If you ride US$ 35 worth of JR Lines addition to that then you will come out as break even with JR Rail Pass.

Cannot ride Nozomi on JR Rail Pass. Nozomi departs Tokyo every 10 min. where Hikari runs twice every hour.

Retrun from Hiroshima, need to transfer at Shin Osaka if you use JR Rail Pass because cannot ride on Nozomi on JR Rail Pass. If you buy each tickets then can ride Nozomi form Hiroshima to Tokyo without transfer.

My meager two cents worth. We were in Japan a few weeks ago. Tokyo and Kyoto area. We didn't buy passes except for single day train passes because our schedule and trip was mostly seat of the pants. The pass was not always the cheapest, but trying to figure out how much and where to go for each leg was made easier by already having the tickets. But one suggestion I have is to use google maps to check some likely itineraries. It is AMAZINGLY helpful giving you the actual train times, places you need to switch lines, and even the cost of some of the legs. That way you can see if a specific pass will work for the various train lines you will need (I think I read there are 30 in Tokyo). Just put in the station names or even hotels and google did the rest.
Of course you will need a data plan once you are in Japan, and note that you can't buy voice SIM cards as a foreigner, but you can buy data and SMS SIMS in machines at the airport. Have a great trip! We enjoyed it immensely.

For a 14 day trip, it might be the case that a 7 day pass could cover all of your longer distance travel. If you plan to spend a chunk of time in Tokyo or another city, you can bunch the longer travel in the middle.

The initial Tokyo to Kyoto transport is after 4 days of landing in Japan so it would need to be a 10 day pass really but that's not offered. The 7 day pass would probably include most everything else except for that initial Tokyo to Kyoto train.

I suspect you've already booked your air travel, but just in case not - it might be worth looking at open jaw between Tokyo and Osaka.

I have an SQ suite from LAX to NRT :) Not changing that, not even if a rifle was pointed at my temple.

Download the Tokyo Subway IOS app (by Tokyo Metro Co). This will give you the fare, transfer info and time taken for any destination in Tokyo.

The app works without a data connection or WIFI.....you can use it in airplane mode on your phone.

Or, you can combine this with pocket WIFI (I use Global Advanced Communications and have had good experiences) and you will navigate like a pro.

You can still have a separate flight NRT-ITM/KIX or vice versa at either end. It can even save you some money and since the trip from NRT to Tokyo Station takes with NEX an hour alone, it can save you some time too.

If you are looking into rail pass for its convenience then don't underestimate the Nozomi restriction. It is little pity that many visitors don't get full experience of the efficiency of the Japanese Shinkansen network because of that. Buying tickets is simple in Japan and for local train trips you can have pre paid IC card which is again more convenient because with rail pass you have to find a manned gate and show it there. I just did a trip in Japan with JR Pass and especially west of Osaka I found it little irritating that quick non-Nozomi connections were not very frequent when there was still multiple Nozomis per hour. Before I had travelled without any rail pass and with regional rail pass that was good on all trains and the overall experience was different.

Many seem to think JR Pass is almost compulsory if visiting Japan but my opinion is that it is not worth is unless you save some real money or you know the restrictions won't affect you (Nozomi and Mizuho Shinkansens operate only west of Tokyo in Kyushu, Sanyo, and Tokaido Shinkansens). And if money savings are important you can save even more by staying in one area.

Also, don't forget the many regional passes that are well constructed for visitors staying longer in one place/area. As Kallio noted, the convenience of more frequent services (ex. nozomi) should not be discarded lightly.

Ex. if you stay in kyushu for 3/5d , kyushu pass is much better (and cheaper) than nationwide.
Or, maybe, the new(ly named) JR Tokyo Wide pass for kanto area.
Or, Sanyo Sanin pass for your JR Sanyo needs (Kyoto-Osaka-Hiroshima-Hakata)

(I think) Full list of passes:
http://www.japan-guide.com/e/e2357.html

JR nationwide on the other hand is worth it for pendulum ( :D ) traveler covering different areas in few days (monday-fukushima, tuesday-hiroshima, wednesday-kanazawa, thursday-kyoto).
Finally, also note that some passes (not nationwide) are available for buying IN Japan the last minute if you don't want to commit before arriving (or if you are waiting for Mr Kuroda's easing).


ps. I've used nationwide, JRSanyo/Shikoku/Kyushu (not available now), Kansai Wide and next time I will try JR Tokyo Wide. It was very easy to calculate which pass was the best with a simple xls and hyperdia.

I agree that often vacation visitors to Japan will not break even using JR Rail Pass. That is the reason there is JR Rail Pass. JR Rail Pass users are very small portion of entire JR riders, less than 5% and some old figures showed less than 1%. Also, majority of JR Rail Pass users actually end up not break even.

That said, as I am self-proclaimed train geek and maybe familiar with JR fare rules, condition of round trip discount, which fare portion discount apply, condition of connection discount, validity of fare, etc. However, even for local Japanese people who commute on JR trains every day fare calculations of JR trains is not that straight forward. Those English websites simply display single ride one way fare. Often does not take in consideration of routing validity, transfer discount, etc. Many those English websites do not know invalid routings.

For visitors who are not that familiar with Japan and do not speak the language, JR Rail Pass is convenient tool. I understand FlyerTalk is about getting first class seat for free, but regardless of if breaking even or not JR Rail Pass is convenient which rid of monetary concerns of how much entire trip will cost. You know how much JR Rail Pass cost and that is the cost of riding JR trains during the visit to Japan.