Japan Rail Pass and Hakone Free Pass

I am planning an eight-day visit to Osaka, Tokyo and Hakone next month and am confused about the Japan Rail Pass (7-day) and Hakone Free Pass and whether or not I need one, both or neither.

I will be arriving at Kansai Airport and will stay in Osaka for 2 nights, followed by 3 nights in Tokyo, 2 nights in Hakone, and 1 final evening in Osaka before returning to San Francisco.

Does it make sense for me to buy the 7-day Japan Railways pass? Should I also buy the Hakone Free Pass to travel roundtrip from Tokyo to Hakone. I understand that the Hakone Free Pass will allow me to travel within the area on other modes of travel, in addition to train.

Does the Japan Rail Pass entitle me to any of those benefits in Hakone?

Thanks for any advice!

The cost for the 7 day JR Rail Pass is nearly the same than the return trip Osaka-Tokyo. So yes the pass makes sense. With the JR Rail Pass you can approach Hakone area as far as Odawara. From there no JR trains, so you will need a Hakone 2 day pass from/to Odawara.

I am planning a 3-day, 2-night stay in Hakone later this month. We'll be arriving in Hakone via train from Tokyo and I am planning to buy the Hakone Free Pass for transportation around the Hakone area. We are staying at the Hyatt Regency.

My questions are:

1. Is the Hakone Free Pass a practical and sensible way to get around Hakone?
2. Is it better to rely on taxis to get around? (I assume that renting a car is not practical.)
3. Is the aerial tram open for visitors in November?

Thanks for any advice!

Is the Hakone Free Pass a practical and sensible way to get around Hakone?

Yes! Hakone is very well covered by public transportation.

Is it better to rely on taxis to get around? (I assume that renting a car is not practical.)

No, generally speaking, taxis are not better. But they can be convenient if you are in a hurry or in a place not well served by public transportation. They are also expensive.

Renting a car is actually a very practical option, assuming that you can get an international driving permit and have the confidence of driving on the left on mountainous roads!It can be very convenient, except on weekends and public holidays when streets and parking areas are often very crowded:
http://www.japan-guide.com/e/e2024.html

Is the aerial tram open for visitors in November?

Yes, all transportation operates around the year.