what time you're landing? I think day 1 not enough time if you wanna land then go check in then go for the romantic train like that
for day 5 you have any particular place you wanna visit? I would suggest day 5 to put only Hakone so that you don't have to rush. you can put shinjuku into day 4. shinjuku and shibuya are like neighbour city
Yes, after Hakone, if time permitted would like to visit the surrounding of Shinjuku.
Looked good at the moment and it's more do-able than previous itinerary. I knew my group (and me too) was too greedy previously that our itinerary was pretty packed everyday. While we managed to do most of them, every morning it's hell trying to get up. Most people will understand this on... the 3rd day onwards hahahaha.
Just some additional comments/ pointers:- Asakusa is really huge, but you'll see shops starting to open from 10.30 to 11am onwards. So even if you leave accommodation early, there's nothing to see yet.
- On Day 3, just take note that Tsukiji starts to close around noon or 1pm, so be sure to arrive early.
- In Odaiba, there are few things to do/ see: visit Fuji TV exhibit, chibi maruko cafe, Diver City's Gundam (check the performance time) and Decks (to see rainbow bridge, statue of liberty etc). So in my opinion, Odaiba is beautiful at night - both the Gundam and night view breath taking.
- Day 4, yes do Meiji >> Takeshita Dori. You can also buy bento/ sandwiches etc and eat in Yoyogi Park. Yoyogi Park is just next to Meiji Shrine. If you don't want to make the detour, then I suggest before going to Meiji purchase your lunch meals. After Meiji, straightaway head to Yoyogi and have a relaxing/ fun picnic. Then get to Takeshita Dori and have the Harajuku Crepes, Zaku Zaku ice cream etc
- Get your Hakone pass earlier and not on the day you're going. Buy in advance and I suggest to top up for Romancecar; it helps you get there faster and earlier. Ask the Odakyu counter about Romance car:
https://www.odakyu.jp/english/romancecar/- Lastly, everyday before leaving the hotel/ house, check the weather forecast. If there will be rain, prepare/ buy an umbrella beforehand. It helps a lot to prepare in advance.
No problem on the water bus, just a recommendation. At least you manage to do 1 way! I will assume you're staying in Asakusa throughout your trip? Wise choice

from Asakusa station, you can get to airport directly (be it Haneda or Narita) without any transit.
However the less-desirable part of it would be: staircase only. It's a pretty long way going down and then up some stairs in that station. There's no escalator nor lift.
Would love to recommend onsen if you could make time but unfortunately it already seemed pack and Hakone is only day trip. No worries, you'll find it slightly easier to plan the next time onwards

All the best and have fun!
I think he probably meant Day 5's night time to visit Shinjuku's Kabukicho. I think by 5 or 6pm, the bus from Hakone to the station is getting lesser. As such, they will have no choice but to leave around that time. Likely to arrive back Shinjuku around 8+ latest. In that case, there's still time to visit Kabukicho for around 1-2 hours and have dinner there.
Besides, Kabukicho gets better the later it is

Thank you so much for all the info, really help me a lot. Do you prefer I start the 2nd and 3rd day with Disney and Hakone or put it at last? You know la the 1st few day the energy is there. I don't know how hot is in August cos I will be bringing my 3yo daughter along, kinda worry about that. Another thing, how long can one spend in odaiba?