Itinerary in Hakone

I will be reaching Haneda at 6 am and intend to head to Hakone directly. I will be staying at a ryokan in Hakonemachi.

Would it be better for me to:

1) Day 1: head to Gotemba, put luggage in locker, shop, go to Hakonemachi & check in (but not sure where to get the 3900 Hakone Free Pass along this route?)

Day 2: Check out at 9 am, put luggage with ryokan, sight-see, go back to ryokan & head to Osaka

OR

2) Day 1: head to Hakonemachi, check in/ put luggage with ryokan, sight-see, go back to ryokan for onsen & dinner

Day 2: Check out at 9 am, bring luggage to Gotemba, put in locker, shop, go to Osaka from Gotemba (how to go to Osaka from Gotemba, preferably using JR pass)?

I personally would go for option 1. Or better: send your big luggage from Haneda to Osaka and bring only a small bag to Hakone.

The Hakone Free Pass can be bought at Gotemba Station.