Does buying a JR pass make sense for my itinerary?

Hi there!

Looking at your itinerary, it is very Tokyo focussed so I dont think a 14 day would make much sense for you.

If you were to use a 7 day Japan Rail Rass (¥28,300) from the 4-7th, you would be able to save ¥3510 per person:

1. Tokyo > Odawara: ¥3840, (35mins, 83km)
2. Odawara > Osaka: ¥12470, (190mins, 472km)
3. Osaka > Kyoto: ¥540, (29mins, 42km)
4. Kyoto > Osaka: ¥540, (28mins, 42km)
5. Osaka > Haneda airport terminal 1: ¥14,420

TOTAL: ¥31810 for 5 legs

Also, as you can start using the rail pass from the 1st of April you will be able to make more savings if you choose JR routes around Tokyo with the Rail Pass instead of the metro (here's a map of JR lines in Tokyo for reference).

On arrival, I recommend you purchase the [Narita Express + Suica metro travel card combined deal]. With the Narita Express you can travel directly into Shinjuku (a great modern rail experience), and also are given a prepaid travel card good for ¥1500 worth of travel on the Tokyo Metro or JR trains. This combined Narita Express return + metro card costs ¥3,500. As the normal total cost of these items is ¥5110, you save ¥1610 if you choose this option. Another way to think about this is that you get ¥1500 of Metro travel for free. You may need to top this up during your time in Tokyo, but this is quick and easy to do as you need it.

Hope this helps!

thanks for the detailed and quick reply, Mari!
It's a lot of help, thanks!