1. As my flight is expected to arrive Haneda at 2305hrs, will i be able to catch the trains from Haneda to Shinagawa ?
What time are the last trains from Haneda ?
You should be able to catch the last Keikyu train which departs at 12:02. It takes 20 min, costs 400 yen, and travels direct to Shinagawa Station.
2. How much does it cost roughly for a taxi ride from Haneda Airport to Shinagawa ?
It takes roughly 25 minutes and 3500 yen by regular sized taxi, not utilizing the expressway.