OK, thanks, but just FYI: I am flying into Haneda (from Manila) and flying out of Narita. I definitely would have purchased my NEX return ticket upon arrival in Narita if I could.

The ticket machines are very easy to use with English menus. They also accept CC but you need to have a PIN. Most machines are for recharging Suica and local tickets. The machines that you want sell reserved and Shinkansen tickets. There should be something in English indicating this. If you are taking JR from Meguro then buy at the first station so that you can use it for your entire trip.

This is getting quite technical but if you have a Suica/Pasmo smart card with remaining value then you can use this card to enter the train system and you then you would just buy the reserved seat supplement from the machine, which is about half the total price. It asks if you only want this during the process. If your stored value is not enough then you can pay the remaining exit fare at Narita.

Also, if you are in a rush then you can get on the NEX without a reserved ticket and buy it from the conductor (or hide in the toilet :0). Similarly, you can take an earlier or later train. The seats never sell out in my experience -- usually half full trains. Exception might be around a big holiday.

p.s. If I were you then I would buy a Pasmo card from Keikyu when you arrive at Haneda.

For the benefit of anyone reading this thread and has a similar question to the OP's, I'm going to post this from the point of view of someone who has traveled to Tokyo three times in the past 12 months and has a basic familiarity with the area and the transit system but does not read or speak Japanese. In my opinion, trying to navigate without the benefit of a smartphone and pocket WiFi is going to have its challenges. You may figure out the correct route to get from Point A to Point B and even the correct exit, but upon exiting a station or building, there are few landmarks that help you get your bearing and it's quite easy to get turned around or headed in the wrong direction. Some of the better restaurants and shops I have visited have been on side streets/alleys that are near impossible to find by street name alone. My wife will give me directions like "Use exit B6, head about block and look for the Dotour cafe and hang a right down the alley, followed by a left down the side street and look for the restaurant on the left about halfway down the block." You're not going to get that from a map or guidebook.

One thing that always gets me on the train and subway lines is that they, like car traffic, run in directions opposite of what a US citizen would expect. So, I will pick the right line, but get on the wrong platform and get on a train headed in the wrong direction. On the major lines, the recorded announcements are in Japanese and English, but if you get on some of the "lesser" lines, they are all in Japanese, so you need to listen carefully to the station names and read them when you pull into the station. Google Maps and other apps are helpful in pointing out which tracks in the station the line runs on and what direction train to take.

Navigating with a paper map or tourist guidebooks can be done, but with some challenges that are greatly reduced with a smartphone or handheld GPS.

Great list, downloading to my iPhone now. Will carry some extra battery chargers and should be golden. Thanks!