Have you confirmed that flying into another airport (e.g. Chubu Centrair [NGO]) cannot be a better option?
I am arriving at Haneda at 8:30 pm on a weekday. It sounds better to plan to stay in Tokyo for that night.
In order to catch Shinkansen Hikari 539
(departing from Shinagawa at 22:07),
i.e. your last chance to travel to Nagoya by railway before dawn,
you have to leave HND International Passenger Terminal by 21:32.
You may miss it
when your flight arrival is delayed much
or when you need relatively long time
to go through the immigration procedure
or to get your JR tickets (= basic-fare ticket and Shinkansen ticket).
Will my ticket from Keikyu allow me to transfer through the Keikyu transfer gate to the JR side so that I can buy my Shinkansen ticket at Shinagawa? Your Keikyu ticket is not valid inside JR ticket gates of (JR) Shinagawa Station.
- Map of (JR) Shinagawa Station
http://english.jr-central.co.jp/info/station/_img/shinagawa_L.jpgAt the Keikyu -JR transfer gate,
you both exit Keikyu and enter JR,
so you need something which is valid for JR.
This transfer gate
is between the Keikyu concourse and the JR non-Shinkansen concourse.
Choosing this transfer gate,
you pass through the Shinkansen South Transfer Gate to the Shinkansen zone.
When you use a PASMO card on the Keikyu lines:
(1) At the Keikyu - JR transfer gate,
you touch that card to the reader-writer device of the gate machine.
(2) At the Shinkansen South Transfer Gate,
you put your JR tiickets into the gate machine,
touch that card to the reader-writer device,
and pick up the tiickets.
Alternatively,
you can exit Keikyu through the Takanawa (exiting) gate,
go up a staircase or escalator to the pathway of the JR station,
walk on the pathway from its west end to around its east end,
and pass through the Shinkansen South | North Ticket Gate to the Shinkansen zone.