Hi, I just got back from Japan few days ago so my fresh memory might be able to help u a bit
Oops! Sorry for my super long post!
1) I can't recommend u family sized room hotel, sorry.. I only went with my hb and we stayed at a "budget" hotel and it was in a very accessible location.. We literally walked everywhere. Do take note that most of these hotels are quite small in size (like hotel81 kinda size but of course much higher quality!).
2) I have tried taking both trains and buses on both my trips before and I must say, I will opt for buses when I go back there again. If your hotel is near the bus stop, it's even better. If not, I know for sure there are buses that go to Tokyo Station which is accessible to everywhere by train. You should check with the Information counter once u land at the airport. They do converse in english and will direct u to the bus ticketing counter which will advise u which is better.
I highly recommend the bus because u won't have to lug your own luggages and barang barangs once u are in the queue, yes even if u bring stroller. The staff will take care of it all for you from the moment u queue all the way to when u alight.. It's such a luxury!
If u're unable to take the bus (maybe due to longer wait time or hotel location nearer to other areas et), u can take the train NEX (i think that's the name. Narita Express). The downside of taking train is that u have to handle the luggages yourself all the way (and it's about more than 1hr ride).. Train rides in town can sometimes get a little packed though.
I wouldn't recommend Taxi at all.. Even their own people also discourage us from taking it, suggesting train/bus instead.
3) If u can tahan walk a lot, u can consider pram. I personally think that strolling in the cool weather is nice. If u're going to be traveling around a lot (by trains), better to use carrier. Most stations are huge and your exit might not have a lift. They really do have killer stairs..
4) There are a few passes and all of their areas are separated. The JR passes are only worth to buy if u're doing extensive traveling outside Tokyo.
But u MUST get the Tokyo Metro Subway Pass (They have 1,2 and 3day passes)
http://jnto.org.au/a-new-tokyo-subway-ticket/. This pass will give u unlimited rides in tokyo central area. I always always buy them. Make sure u buy enough because they only sell it at the airports, for tourists. On my previous trip, we didn't buy enough so had to go all the way back to buy (yes, that's how value for money this is).
*Important*
As for the JR passes, do u have any itinerary to share? I bought JR Kanto 3day-Pass for my recent trip.
http://www.jreast.co.jp/e/kantoareapass/
Managed to see sakura, snow and beach all around Tokyo outskirts with only this pass
This is a really value for money pass which not many people know of though.. Mainly because it's sold in Japan, again only for tourists (the locations are stated in the site, mainly airports)
Things to take note of:
* Buy all the passes u need from airport once u land. (Screenshot all the pictures of the passes and show to the staff at the airport)
*Important*
* Bring passports (or 1 is enough I guess?) along if u're going to do some shopping at malls. A lot of these places have tax-free for tourists above 10k yen, I believe.
* I like to use this site that gives very detailed info on train lines and even schedules.
http://www.hyperdia.com/ *Important*
* I also like to check out this Japan Guide site to help in my planning of itinerary.
http://www.japan-guide.com/
* Screenshot every info/detail u find. Pictures, names in Japanese etc.. Easier to flash pic than trying to explain to get directions.
*Important*
* If worse comes to worst, use Google Translate! Haha.. I had to use it a few times, especially in the rural areas.
* If u would like to have wifi everywhere u go (like we do), can rent pocket global wifi from here
https://www.changirecommends.com/owifi.aspx
We used this literally everywhere we went. I know wifi is easily found in Japan but it's not easy when we have to move around and away from those spots. This little device is extremely useful when u need to know which direction to walk once u alight the trains.. =P Google Map + Hyperdia is the best. Gets u anywhere u want to go.
Sorry again for the super long post.. =) Hope the info I gave is useful~