Wakayama Line and Best use of jr pass to Hakone

Hi there!

Here are some answers for you:

1. Yes, you can use the JR Pass to get to Wakayama. If you're travelling from Osaka you can use this sample itinerary to get to Wakayama.

2. To get to Hakone from Osaka using the JR Pass you can use the JR Pass to get to Odawara on the bullet train. From Odawara you'll need to get the non-JR Odakyu lines (possibly using the Hakone Free Pass. Here's a sample itinerary from Osaka to Odawara for you.

Hope this helps!