travel between cities (trains)

Hello,
I've been doing research but there is so much information when it comes to figuring the best way to travel between cities. Any help is really appreciated.

I start off in Tokyo, hotel is close to Shinjuku Station.
I then go to Hakone for just 1 night (Yama No Chaya onsen).
From Hakone I go to Kyoto for 2 nights - staying near Downtown Kawaramachi.
Then 2 nights in Osaka, near Namba (plus a quick day trip to Nara).
From Osaka I will meet friends in Okinawa so I spend one night there, then back to Tokyo (two separate flights, no trains. Itami to Naha, then Naha to Haneda airport). Finishing my trip in Tokyo.

There is a lot to consider.. does it make sense to buy a 7 day JR pass? Should I get a Hakone Free Pass?
No matter what I know I need a Suica card.

I know my trip is way too packed.. but I have limited time and I really want to see all these areas.
Thanks for help!

seven day rail pass wont pay off.

yes hakone free pass (odawara version) is a good idea. if you do the full tourist loop.

yes suica card is a good idea for small train and bus trips.

i would suggest just staying in one place for Kyoto/Osaka. They are only 25 minutes apart.

I agree with Hakata 14, best to stay in either Kyoto or Osaka as they are so close together.

You won't get value from a 7 day pass, but you might benefit from one of these one-way discount packages from Japanican, if you want to stay in Kyoto. https://www.japanican.com/en/tour/list/?so=c&typecd=TOU&typegrpcd=TPA&...