My Hakone Itinerary - too packed?

Hi! Here's my itinerary for March 27, for my trip to Hakone (from Akiba). Do you think this is too packed? Thanks!

745AM Ochanomizo or Akiba, train to Tokyo

826AM Tokyo shinkansen to Odawara (Kodama 639)

900AM Buy Hakone free pass at Odawara Stn

915AM Odawara castle

945AM Odawara Station to Hakone Yumoto (by Hakone Tozan Railway? Odakyu?)

952AM Hakone Yumoto to Miyanoshita (by Hakone Tozan Railway)

1025AM Miyanoshita lunch

1100AM Miyanoshita to Chokokunomori (by Hakone Tozan Railway)

1100AM Chokokunomori Bijutsukan (open air museum, Y1400 per person aft discount)

100PM Chokokunomori to Gora (by Hakone Tozan Railway)

120PM Gora to Sounzan by Cable car

130PM Sounzan to Togendai (beside Ashinoko) by Ropeway

200PM Togendai Ashinoko to Hakone to Moto-Hakone [no boats? bus back to Odawara]

230PM Moto-hakone to Odawara by Odakyu Hakone Highay bus

342PM/411PM/437PM/442PM Odawara to Tokyo by Shinkansen (Kodama/Hikari)

510PM At Tokyo

I only read as far as Odawara Castle and it already became clear that the itinerary is not realistic.

Your shinkansen arrives at Odawara at 9:01. By the time you have purchased the Hakone Free Pass it will be 9:05 at the very earliest. More likely 9:10. The castle is a ten minute walk from the station, meaning you arrive there around 9:20 and in order to catch your 9:45 train would have to leave around 9:30, giving you 10 minutes to see the castle. Unless you just want to take a quick look from the outside, this is not enough time. Depending on personal pace of travel, Odawara Castle requires 30 to 90 minutes.

I now looked at the rest of your day, and it doesn't look too bad.

945AM Odawara Station to Hakone Yumoto (by Hakone Tozan Railway? Odakyu?)

The section between Odawara and Hakone Yumoto is owned by Hakone Tozan Railway, but the trains operating along it are Odakyu trains. (Hakone Tozan is a member company of the Odakyu Group.) For the user, it doesn't matter.

952AM Hakone Yumoto to Miyanoshita (by Hakone Tozan Railway)
1025AM Miyanoshita lunch

There is something wrong with your times. If you depart Odawara at 9:46, you won't arrive in Yumoto until 10:03 and in Miyanoshita 10:37.

35 minutes is a short time period for a lunch even if you know what restaurant you will be going to. Even more so if you don't and still have to find one. Of course, it also widely depends on the type of lunch.

1100AM Miyanoshita to Chokokunomori (by Hakone Tozan Railway)

My guess is that the average traveler wouldn't make it to the Chokokunomori Bijutsukan until around 11:30. I understand they have a restaurant...

At least, however, you allocate a lot of time to the museum.

200PM Togendai Ashinoko to Hakone to Moto-Hakone [no boats? bus back to Odawara]

Why no boats? I recommend to complete the round course by taking a boat to Moto Hakone and then take a Hakone Tozan bus (not Odakyu Highway Bus!) back to Odawara.

Boat schedule:
http://www.hakone-kankosen.co.jp/foreign/en/