Use JR pass or separate passes

Hello,

We are three adults going to Japan for the first time from may 17th-June 23rd. First I was going to get the JR pass then I looked at many other passes and tickets for the different cities we'll visit and now I'm a bit confused as to whether the JR pass is worth it or not. Here's our itinerary:

23/5 arrive in KIX (our hotel is in Nankai Namba station)
24-27/5 around Osaka (Osaka castle, Universal Studios, Tenjinbashi-suji, etc)

28/5 Arrive in Kyoto
we'll stay for 5 days in Kyoto visiting Gion, Higashiyama, Arashiyama (plus the Sagano Scenic Railway),etc and we'll go on side trips to Nara and Hiroshima.

2/6 Arrive to Tokyo by Shinkansen
In our time in Tokyo we'll explore the city and visit it's many areas and attractions in addition to Disney Land/Sea. (we won't stay there though)
The side trips we'll do from Tokyo will be to Yokohama, Kamakura and Hakone.

17/6 Departure from Narita Airport

So I want to know if getting a JR pass is a good choice. And if it is, which one? Because from what I read, we won't use it a lot for inside Kyoto since buses and walking are enough there. Are Kyoto buses covered by the pass to fully utilize the pass there?
or should we get a JR regional pass?

Also, if JR pass isn't a wise choice, then what other passes are good? I found a lot of good passes for Kansai/Kyoto/Osaka and Tokyo (like the free kippu) but most of them are for a maximum of 4 days only.

Another question that I didn't find an answer to which are the timings of JR trains, when is the first train and last train to go daily?