Osaka-Tokyo-Hakone OR from Osaka-Hakone

Hey guys,

I have been reading a lot on forums however cannot seem to find a clear answer in regards to what would be the best way to travel to Hakone from Osaka.

Our itinerary is:
24th to 28th Dec- hotel booked in Osaka
28th Dec- one night at Mount view hotel booked in Hakone
29th Dec- Shinjuku, Tokyo hotel booked for 29th Dec to 2nd Jan.

Some people seem to recommend taking the Shinkansen from Osaka to tokyo, then from Shinjuku station to buy the Odakyu Hakone 2-day pass with return trips to Shinjuku to cover our overnight stay in Hakone. However wouldn't this just add extra travel time and be more expensive? I am also worried about our big luggage..

Should we instead take the Skinkansen to Odawara station and then just purchase the hakone 2 day pass there plus another single romance car trip to Shinjuku to return to Tokyo on the 29th?

I would really appreciate any suggestions on the above. Thank you!!

I did the Shin-Osaka to Odawara via Shinkansen Hikari, it took 2 hours 20 minutes. Then bought the Hakone Free Pass in Odawara. I think it is faster and cheaper than going through Shinjuku.