Hakone - Can this be done?

Please excuse the wall of text that follows, I've been planning to excess!

My boyfriend and I are going to Japan for the first time in December and we're spending a night in Hakone while we're there.

It'll go like this:
Dec 3 (THU) - Arrive in Hakone, check-in at ryokan (15min walk from Hakone-Yumoto station/5 minute walk from Tonosawa station) and explore the town before having a dip in the hot springs and eating dinner. Stay overnight.

Dec 4 (FRI) - Eat breakfast at ryokan, check out. Leave Hakone and go to next destination (Kyoto - unattended airbnb-style townhouse accomodation approx. 10 minutes walk from Kyoto station)

However, our Kyoto place isn't open until 4pm so we can't send our bags ahead, therefore I thought we could leave our bags at the ryokan and go explore a bit before heading off on our next journey. I have some ideas about what I want to do, but with bus schedules and the like, I have no idea if it's too jam-packed. If someone with more experience with the area, buses and time it takes to get things done could tell me if this is doable, I'd be most grateful!

Main attractions:
- Old Tokaido Road
- Cedar Avenue
- Hakone Checkpoint
- Lake Ashinoko

Breakfast: 8.00am – 9.00am
Check-out: no later than 10am (leave bags at ryokan)


Ryokan to Hakoneyumoto Station
- OPTION 1: Walk from ryokan to station (15 mins)

- OPTION 2: Walk to Tonosawa station (5 mins) - Take train to Hakoneyumoto (4 mins)


Hakoneyumoto Station to Hatajuku
Bus from Hakoneyumoto Station to Hatajuku Bus Stop (35 minutes) (BUS LINE K)


Hatajuku to Moto-Hakone
Walk from Hatajuku Bus Stop to Motohakone Bus Stop via Old Tokaido Road (100 mins max.)


SIGHT-SEEING
- View Lake Ashinoko from Moto-Hakone


Moto-Hakone to Hakone-Machi
Walk from Motohakone Bus Stop to Hakonemachi Bus Stop via Cedar Avenue (10 mins)


SIGHT-SEEING
- View Lake Ashinoko from Hakone-Machi
- View Hakone Checkpoint


Hakone-Machi to Hakoneyumoto Station
- OPTION 1: Bus from Hakonemachi Bus Stop to Hakoneyumoto Station (60 mins) (BUS LINE H)

- OPTION 2: Bus from Hakonemachi Bus Stop to Hakoneyumoto Station (15 mins) (BUS LINE R) (I know this one is rare)


Hakoneyumoto Station to ryokan (RETRIEVE BAGS)
(15 mins max)


Ryokan to Hakoneyumoto Station
(15 mins max)


Hakoneyumoto Station to Odawara Station
Take train from Hakoneyumoto Station to Odawara Station (15 mins)


Odawara Station to Kyoto Station
Take train from Odawara Station to Kyoto Station (190mins max.)


Kyoto Station to townhouse
Walk from Kyoto Station to Kyoto townhouse (10 mins)



My prediction:

Travel time* + 60 mins assumed faffing about /sight-seeing
480 mins + 60 mins = 540 mins/9 hours
*assuming most time-consuming route

Assuming we leave at 10am on Hakone Day 2, we will reach the Kyoto townhouse by 7pm.

Extra notes:
We will have a JR Rail Pass and a 2 day Hakone Free Pass, so everything should be covered by that.


Thanks again, sorry this is so damn long and if the formatting isn't quite right! I would really, really appreciate some help!

I do not know much about the bus timing but I would just walk about the hotel in Hakone, have lunch in Hakone town. Take transport to Kyoto. Do some light sightseeing nearby the station or light shopping in the station. Head off to the kyoto hotel.

Or

Just store the luggage at Kyoto station luggage room or lockers.

The math add up right but if you travel like this you will be very tired at Hakone!

For a typical ryokan, breakfast is usually starts at 7am so may be you can get up a bit, one more bath and enjoy the B, then check out a bit earlier. The hakone yumoto station has locker service, you can check as you arrive this station on the dec 4th and determine if you want to use this (subject to size constraint and availability on 5th), then you save half an hour retrieving your bags.

Rest just follow your route. The line R I think is for weekend (yours is Friday) and is fast!

Motohakone has nothing to see there, save your time and walk straight to Hakone machi.