Hakone trip questions

We are a family of 5 (2 adults, 3 children 10, 12 & 14) travelling in October. We intend to travel from Kyoto (by Shinkansen) and buy a Hakone Free Pass at Odawara Station, we will then carry on to Tokyo the following afternoon.
I would like your thoughts on whereabout on the round trip to stay overnight and perhaps recommendations for mid-price child friendly hotels?
Also, does anyone know if we can leave the bulk of our luggage at Osawara station as we are travelling between rental apartments so cannot forward luggage hotel to hotel. Thanks you in advance.

I recommend that you stay overnight in the Japanese style inn located in Hakone. That way, you will be possible to put the luggage in there, then you go out to Hakone sightseeing.
In the Japanese-style inn, you may have to stay in Japanese-style room, and sleep using the futon instead of a bed.
http://www.japaneseguesthouses.com/ryokan-search-results/?area=Hakone&...

I would recommend staying at either Fujiya Hotel or Yunessun Inn.

Fujiya Hotel is one of the oldest, most renowned hotels in Japan and they have great rates specifically for foreigners.

The Yunessun inn is connected to a popular water park which would be a great activity if you have kids!

Link for Fujiya Hotel http://www.fujiyahotel.jp/en/stay/index.html

Link for Yunessun Inn http://www.hakone-kowakien.com/english/

We left our bags in large lockers located at odawarra station. They are located on in two or three places around the station and about 600 yen per bag. Cheaper than a hotel.
We travelled from Tokyo to Hakone and then went onto Nagoya.

I am thinking of doing a one day trip from Tokyo in May.
Does anyone recommend a clockwise or anti-clockwise itinerary ?
How many hours should I allocate for a round trip since I need to plan what time I should leave Shinjuku.
Thanks in advance.