Hey All,

I'm starting to plan a trip to Japan this spring with rewards points in economy with United miles. I want to choose a flight itinerary within the next 2 days so the saver rewards don't disappear while I'm waiting around indecisively.

Here are the departure options that I'm torn between for my travel dates. They both have the same mile + $ cost.
Option A: Nonstop JFK to NRT on ANA
Depart 6pm Saturday, arrive 9pm Sunday
Travel time: 14 hours + 4.5 hours ground transportation

Option B: JFK to YYZ to HND on Air Canada
Depart 10:30am Saturday; 1.5 hour transfer; arrive 3:40pm Sunday
Travel time: 16.25 hours + 3.5 hours ground transportation

Pros of option B:
1)HND is a lot closer to downtown Tokyo
2)Arrive with time to settle into my accommodations, get dinner, venture out for a SIM card, and have plenty of hours to sleep and adjust to the time zone shift
3)It sounds like Tokyo shuts down super early compared to what I'm used to in NY. The last train headed downtown from NRT leaves at 10:37pm, and a taxi costs a whopping $200. I don't want to get stranded at the airport if my flight is delayed and/or customs takes a long time.
4)I might feel a bit vulnerable walking alone with a large bag at night if the streets are empty when I get off the train late at night. I Don't want to pay for a taxi if I don't need to.

Cons of option B:
1)Chance that a bad delay of the first flight could cause me to miss the second flight
2)2 hours longer overall travel time
3)General airport hassles 3 times instead of 2

Which do you think is better? I'd be interested in hearing from people familiar with these routes or people who chose the connection in similar situations.

Also, is there any significant difference in food/IFE/comfort between AC and ANA in economy for this route?