We used the pass and stayed in Hakone on the last stop. Just the transport from Odawara station is 1500yen each way then if you do one activity it pretty much pays for itself. We took the pirate ship to the ropes (cable car) went all the way to Gora , took the bus to the Gora Park then took the bus back and it was all inclusive in the Freepass. We got the 3 day one as it was only 400yen more from memory but worth it

I guess things will be better by the time you visit next week but this is what's happening right now ~ The Odakyu Odawara Line, which connects Tokyo's Shinjuku Station with the Hakone area, is interrupted between Hadano and Shin-Matsuda Station until further notice. Substitute buses are running, but there will be delays. The Romancecar is not running. Consider using JR trains from Tokyo to Odawara, instead (but note that the JR trains are not covered by the Hakone Free Pass). The tracks of the Hakone Tozan Railway were badly damaged, and trains will remain out of service between Hakone-Yumoto and Gora for an extended time period. The Hakone Cablecar suffered some damage, but is scheduled to resume operation from October 17. Many road sections remain closed. As a result of the road closures, many bus lines are out of service. Buses resumed service today between Hakone-Yumoto, Moto-Hakone and Hakonemachi via the Hakone Shindo road, and the Odakyu Hakone Highway Bus is running between Shinjuku and Togendai, but most other bus lines remain out of service. Despite the big impact on transportation, many tourist spots have reopened. Unrelated to the typhoon, the Hakone Ropeway is currently closed between Sounzan and Ubako due to a volcanic no-entry zone.

According to the travelwithamnet blog, as of Sept 25, 2019, only part of the ropeway has reopened ie between Ubako Station and Togendai Station. A further quote from the blog: "There is still a no-entry zone maintained for Owakudani, and the ropeway remains closed between Ubako Station and Sounzan Station. In order to compensate for this inconvenience, there is a substitute bus service running between Togendai, Ubako, and Sounzan." Togendai Station is where the Lake Ashi cruise ships dock and Ubako Station is the next station up Mt Hakone from Togendai but its not all the way up (ie to Owakudani) but from Ubako, you can still get a good view of Lake Ashi and if there are no fogs, you might see Mt Fuji. I do hope and pray that by the time you visit in December 2019 the entire ropeway will be reopened for your enjoyment. Keep the faith!

Closed indefinitely due to seismic activities. Not only does this affect the Ropeway, it also affects Owakudani. Unfortunately no word on when these attractions will be re-opened.

I was reading your question again and have a couple more thoughts. So first, assuming that the ropeway is operational during your visit, your plan to visit the Hakone Open Air Museum first is a good idea although I would recommend starting early and try to get to the museum at 9 am when they first open. It’s not so crowded and you have the option to spend a bit more time there. It’s also quite an experience going up the mountain riding the Tozan railway from Hakone Yumoto station to the museum. From the museum you can then catch the Tozan railway to Gōra to ride the Tozan cable car to Sounzan to ride the ropeway to Owakudani and then from Owakudani continue on the ropeway to Togendai to catch the Lake Ashi cruise to Motohakone ko. At Motohakone ko if you have time you can walk to nearby Hakone Shrine before going back to Motohakone ko to take the bus back to Odawara to go back to Tokyo. Pls check the bus schedule. That is one way round the Hakone ‘loop’. That was how my family and I did the loop but we started our journey for Odawara. You can also do things in the reverse direction but the Museum closes at 5 pm and it’s also usually more crowded in the afternoon. Again I recommend that you find out if the ropeway is operational.

We were there in April and all was fine. I think if it’s extremely windy they may stop it running. Maybe check volcanic activity in the area but I believe if it’s possible to run it they would as it’s a great tourist attraction. Hope that helps

If only one section is closed.dont miss. If all is closed and you can get to owakundi by bus. I would still recommend

Check their website. Better yet email them to find the latest information. Don’t speculate or ponder. Things change quickly.