should I get JR pass for this itinerary?

Hello there,

I checked your itinerary for the best route and I would recommend buying normal tickets for your travel. The JR Pass makes sense if you travel longer distances or a couple of times on the Shinkansen. In the above itinerary long distance travel is limited to a one way Kyoto - Tokyo and for this I would recommend normal tickets.

For your arrival at Kansai Airport, consider the ICOCA + Haruka package. It provides you with a discounted ticket on the Haruka to Kyoto and also gives you an ICOCA card which is a prepaid travel card and very handy for local travel around Kansai and Tokyo.

Hope this helps!
Daniel