How long would 'this' take on a Japanese train?

Question:

I am checking up on what train passes I'm going to use and I came upon a pass for local and rapid train. So my question is, how long would it take using local/rapid (if possible, I don't know their railway rules) to get from Shijuku to somewhere in 1)Hokane and 2)Nagano? Shinjuku would be point A and the other two would be points B.

Answer:

Shinjuku to Odawara (the entrance to Hakone) would take 96 minutes by direct Odakyu Railways Express trains (no extra fees required for Odakyu express trains). It takes between 70-80 minutes by reserved Limited Express "Romance Car" (Extra fee required). This trip is covered by the HAKONE FREE PASS. However you need to pay extra for the romance car, even if using the Hakone free pass.

If you took JR trains instead of Odakyu (Odakyu is better for this route anyway) but if you took JR rapid or local trains from Shinjuku to Odawara, with 1 or 2 transfer it can be about 90minutes as well, but the cost is higher. Odakyu railways is cheaper for the Shinjuku-Odawara-Hakone trip, it's faster and more direct then JR trains.

From Shinjuku to Nagano by JR Rapid and Local trains only will take nearly 400minutes (about 6.6 hours) and require about 3 train transfers if you took local/rapid trains only.