Hakone Pass

1. Does the 2 day Hakone pass purchased from Shinjuku (5000 yen) includes a return leg of trip back to Shinjuku Station?
2. I am planning to only do a day trip to Hakone - is there a one day pass?

Will option 1 be cheaper than purchasing individual tickets for a one day trip?

Yes includes Shinjuku - Odawara one time, Odawara - Shinjuku one time and as many rides as you want to HakoneYumoto and within the Hakone area.
See: http://www.odakyu.jp/english/freepass/index.html
There is no cheaper one day pass, but when using cablecar, robeway, ship and bus one time only during one day round trip the Hakone Free Pass 2 days is already slightly cheaper than single tickets.

do i buy the Hakone Free Pass + Romancecar from the ticketing machines at shinjuku station or do i have to get from Odakyu Sightseeing Center? Because I intend to take the 7am train and the sightseeing center only opens at 8.00am.

can i check if i purchase the hakone free pass at the shinjuku station, will i be able to use it on the shinjuku-hakoneyumoto ride?

I am travelling to Hakone from Toyko before going to Kyoto from Hakone.
Should I use Hakone pass from Shinjuku and forfeit return ticket to Shinjuku and start JR pass from Hakone to Kyoto? Or Should I use JR pass starting from Shinjuku to Hakone?

Very confused. Please help!

Thanks

if i purchase the hakone free pass at the shinjuku station, will i be able to use it on the shinjuku-hakoneyumoto ride?

Yes.

I am travelling to Hakone from Toyko before going to Kyoto from Hakone.
Should I use Hakone pass from Shinjuku and forfeit return ticket to Shinjuku and start JR pass from Hakone to Kyoto?

If you have a Japan Rail Pass, you should use it on JR trains to get to Odawara and buy a Hakone Free Pass from there.