Trip Yokohama to Hakone area

Hi, we are visiting Yokohama in October and I'm planning a 2 day trip with an overnight stay in Hakone Yumoto as we'd like to do the Hakone 'circle' as follows...just looking for advice if this plan sounds OK:

Depart Yokohama on the Shinkansen to Odawara Station.
Take a local train Odawara to Hakone Yumoto.
Take a bus from Hakone Yumoto station to Moto Hakone pier.
Get on the pirate ship cruise up Lake Ashi, disembark at Togendai
Take the ropeway up to Owakudani, then down on the cable car to Gora
Visit the Open Air Museum, then take the local train back down to Hakone Yumoto, where we have booked a ryokan for the night.
Next day, take the train from Hakone Yumoto back to Odawara, then get the Shinkansen back to Yokohama.

Is it best to get a Hakone Freepass from Odawara station to do this? I appreciate this doesn't cover the Shinkansen, but assume it will cover all the other elements of travel (local trains, buses, cruise and ropeway/cable car)?

Can we get a bus from Odawara straight to Moto Hakone or do we have to go via Hakone-Yumoto station?

Is there an easy way to work out the train and bus timetables - I've had a look online at some of them and I'm not totally sure!

We'll have minimal luggage - backpacks only - so I think we'll either take them with us, or leave in lockers at Hakone Yumoto (or drop them at the ryokan on the way).

Thanks in advance!

I doubt that Shinkansen is the best way to travel from Yokohama to Odawara, unless your hotel is in ShinYokohama. Which I would advise against as it is a gdeadh part of the city. There are sufficient local trains to make the trip to Odawara

Regarding your luggage, even if it is small I would either store it in a locker (you are coming through Hakone Yumoto station again, or potentially you can ship it for same day delivery from Hakone Yumoto to your Ryokan.

Plan to get to the ryokan reasonably early (eg 16;00) to enjoy everything it can offer.

If you buy the Hakone pass from Odawara you can get g travel back to the open air museum on Day 2 if you didnft have enough time on day 1 to see it.

Regarding the departure times, I kind of never looked into this. The loop just seems to circle around effortlessly. Never too much waiting.

I would definitely try to visit Owakudani https://www.japan-guide.com/e/e5203.html note that you need a reservation. I went once 20+ years ago and I still vividly remember it. Itfs a unique feeling to stand on a volcanic field that is boiling and moving and small if below your feet. It was off limits for the last many years due to fears of eruption and I havenft been back, but very much in my to do list.

I see no real issue with the plan. You are just doing the loop in reserve or clockwise direction. You'll dodge most of the crowding this way also.

Yokohama to Odawarra using Shinkansen. Seems overboard unlesss you have JR passes and they are free. Otherwise a locao or rapid JR train is a third of the cost and take one hour.