I can Bet with you, By Taking Train from Haneda to Naka-Itabashi success rate are 0%

AAX reach Haneda 10 times out of 8 times been told by Control Tower using Runway 23. If landed at Runway 23 Even U touch down at 10:30...Taxi from Runway 23 to International Terminal need 30 Minute. Means you reach Gate by 11:00, Clear Custom / etc all stuff...Fastest you can go out from Airport are 11:40 ~ 12:00. Means you will missed all Public Transport that leaving Haneda. Even Let you catch the last Train leaving Haneda. Maximum you an go also Shinagawa // Hamamatsucho Station only. 
If you are lucky, Not Landing at Runway 23, Everything good. You should able to catch This Bus to Ikebukuro.
23:25 are Last Bus to Ikebukuro Station. Reach Ikebukuro Station around 00:15.
Ikebukuro to Naka Itabashi Station are Tobu Tojo Line
Last Train Leave Ikebukuro are 00:45
Because you are 1st time to Haneda plus 1st time to Ikebukuro Station, I est your success rate by this method 30%
You Sleep On Haneda Airport Rate are 70%

wow, I'm flying with ANA to Haneda Airport landing on the same hours 10:30PM too. This makes me worried if it delayed, I gona miss the bus to Ikebukuro too.

You Sleep On Haneda Airport Rate are 70%

serious, why nobody shared their AAX 10:30pm arrival experience?
whether they managed to board the last train or not...
just share here la

i myself managed to
1) bought the tokyo metro pass... ~11:00pm - 12:00am
2) board the train from haneda, not sure it is last train or not. boarding time ~12:00 - 12:30am
->(forget the exact time) but the range is correct

but the catch is... my arrival date is on the Chinese New Year's EVE
superduper peak season

so what is your?

bring sleeping bag...

 

Thank you guys for all your advices. At least, you make me aware of what lies ahead so I can be prepared, psychologically..
This is what I get for choosing cheapest airbnb possible. It's ~rm298 per night house for my whole family.. 
I think many have no problem catching a last train to city, except for my case, I'm bit a further away from the city.  I may not be able to catch the last train on a 2nd transfer..

i travelled with hubs n 7months kids. with the normal seat. not that cramp. unless your body size is 

i received a call from AA regarding next week kl<--> osaka flight delay, asked if i want to change the travel date or refund

the call legit or nt?

Wait,isn't the collection counter is open 24 hour?

Delay how long? Usually delay they won't call lik tht one

Delay how long? Usually delay they won't call lik tht one

Alrrady being notified for months...
I forgot original flight time, they changed to morning 8am
Now, few days before flight, asked me do i wan change travel date or refund

Morning Flight to Haneda was Dream flight
Means you reach Tokyo by noon. No public transport problem

I prefer night flight tho. No need to worry about sun blaring at my eyes when i rest or play with my phone.

yup... dream flight