18 day trip, landing and taking off from Tokyo. Should I start with Osaka/Kyoto?

Hello everyone, I've just started organizing the trip I'm taking this October with my girlfriend and I already have a doubt.

I land in Tokyo Haneda on October 3rd and leave from here on October 22nd. I land at 3pm and take off at 12.30pm.

In your opinion, to limit travel with suitcases and check-in / check-out, could it be a good idea to start from Osaka/Kyoto?

The alternatives I have in mind are:

1)

3/10 to 5/10 –> Tokyo

6/10 –> Hakone (reservation at ryokan)

7/10 to 15/10 –> Kansai + Daytrips, staying in Osaka (Nara, Kyoto x2, Hiroshima, Kobe)

16/10 to 22/10 –> Tokyo + Daytrips (Nikko + others to choose)

2)

3/10 –> train to Osaka

4/10 to 10/10 –> Kansai + Daytrips, staying in Osaka

11/10 –> Hakone (reservation at ryokan)

12/10 to 22/10 –> Tokyo

I have already booked the ryokans (both today, and I will immediately cancel the unhelpful reservation) because they seem to be full immediately, so I would organize myself based on this constraint.

Thank you all 😁

by Ok-Chance7997

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