Originally Posted by dvs7310

1 & 3) HND is much closer but depending on your hotel location it may not necessarily be more convenient if using the train. The transit points are different, from Haneda it's Hamamatsucho for Monorail and Shinagawa for Keikyu. From Narita it's Nippori/Ueno for Keisei and Tokyo Station for JR (which also continues around to Shinjuku if stsying on that side.). Don't worry about the arrival time of NH at NRT, you'll have more than enough time to make one of the trains, I've arrived on the late flight from ORD several times, it's quite similar. Tokyo doesn't shut down early at all once downtown. Plenty of 24 hour food and many regular shops are open till 10.

2) You're not going to get a sim card without a Japan residence card anywhere downtown. Get one at the airport that are for tourists. Several places have them, forget if they are rental or for sale.

4) Japan is incredibly safe, on par with Singapore. No one is going to be interested in swiping your bag. The old story about dropping your wallet here and someone will turn it in to the nearest police station with cash still inside is pretty much true.

Whichever route you decide, you'll be ok. I think I'd personally go with AC in your case just because the arrival time in the afternoon is more convenient to settling into an opposite time zone, but if you end up on NH don't worry.