Osaka- Narita vs Hakone- Narita which one easier with kids+ baggages?

Hi
I am travelling with two kids for the first time to Japan on 27th March.
my current itinerary is:
Day 1-5 Tokyo ( one day trip to Nikko)
Day 6 (activate JR pass) Hakone
Day 7-9 Kyoto ( one day trip Nara)
Day 10-11 Osaka
Day 12 taking train to Narita (flight at 10 pm)

I retrospect I should have done it the other way around, starting from Osaka and ending in Tokyo,
So I do not have to travel 3.5 hrs by train to Tokyo before our long flight back home. My Tokyo hotel
Reservations can't be changed but I can do
Tokyo- Kyoto - Osaka- Hakone

But again I think although distance wise Osaka is further away from Tokyo, but it's a simple straight trip
Rather than Hakone that we have to change couple of trains and buses with our baggages
Any help is greatly appreciated

If I wanna go from Hakone to Narita what is the most convenient route ( with baggage)
Thanks
Mariam