Advice on itinerary with 8 month old baby

Hello. I'm planning a trip with my family to Japan in early April 2018. We are a group of 6 adults and a baby( 8 months at time of travel). I would appreciate any input you can give me to make my travel easier. This is our first trip to Japan. I would like to cover a lot of area but not do a hectic trip as I'm travelling with a baby. Could you please review my itinerary and make suggestions?
Day 1- Arrival in Tokyo.
Day2,3,4- Sightseeing in Tokyo
Day 5- Day trip from Tokyo to either Kamskura or Nikko( what would you recommend?) Night in Tokyo
Day6- Leave for Hakone- overnight in Hakone
Day 7- sightseeing in Hakone- overnight in Hakone
Day 8-Leave for Kyoto
Day9,10,11- Sightseeing in Kyoto
Day 12-Day trip to Nara, overnight in Kyoto
Day 13-Day trip to Himeji, overnight in Kyoto
Day 14- Leave for Takayama. Overnight Takayama
Day 15- Sightseeing Takayama
Day 16-Day trip to Shirakawago
Day 17-Back to Tokyo. Leave Japan

1)Does this itinerary seem doable with a baby?
2) Alternatively should we to Takayama after Hakone and then go to Kyoto? That way we can fly out of Osaka? Which would be less travel and more convenient?
3) Are there any additional places or alternative places you would recommend we cover?

Thank you in advance!

It is not a rushed itinerary, so if baby issues arise, then it shouldn't cause too many issues.

Suggestion for a baby of 8 months is to buy one of those chest carriers. Japan is quite pram unfriendly. And by using the carrier, it does free up your hands for other things.

Thank you for the reply.
As an alternative I was wondering if I can base myself out of only two cities( Tokyo and Osaka). We will have luggage with a baby and travelling to multiple locations with it might not be easy.
I would like your opinion on the following
1) From Osaka can I do multiple day trips to Kyoto and cover one part of it each day. I will buy a JR pass.
2) Similarly from Tokyo itself do one day trip to Hakone and another to Fuji five lakes area on separate days.
I was thinking this way I can mix my city sightseeing days with day trip days.

I really like the idea of having two locations and taking day trips from there. I spent nine nights in the Osaka/Kyoto area in November and never ran out of things to see.

I don't know about your 8 month old, but I know at 8 months old, mine needed to nap 2-3 hours a day and preferred to do it somewhere very dark. She didn't give up napping until she was 4.

I think unless yours is good at sleeping in a carrier or good at sleeping on trains, the idea of two main locations and day trips might make sense. I definitely agree with @Hakata14 about using a baby carrier vs. a stroller.

If you can afford it, I think staying in Kyoto and commuting to Osaka would be better. Depending on your child's sleep schedule Kyoto is a lot more interesting to sightsee than Osaka which I would easily skip if I didn't have friends who lived there.

On the Japan Travel sub on Reddit yesterday there was a trip report by someone who had travelled with a baby, giving a review of their trip and tips for baby specifics. Perhaps consider reading that thread - it was quite detailed.