Maybe I try to help since I notice no one reply to you ... check the cost of the train tickets (basic fare + limited express)
http://www.hyperdia.com/en/https://www.westjr.co.jp/global/en/Also, I suggest you stay at Osaka for the last night (or the last few days), so you can do final shopping and pack the bags, rather than carry the stuff you buy at Osaka on arrival, all over Kansai area.
e.g.
D1/2 - ICOCA & Haruka package one way to Kyoto (2000 + 1600) = 3600 yen. Buy at JR Kansai office, now got Hello Kitty edition.
D3-4 Check train cost to Nara. Else get Kansai Thru Pass 2 days.
D5-9 - use the Kansai Wide Area Pass
The Wide Pass is 8500 yen book online, which you can buy in KL for RM340 in Nov'16. Bring receipt and claim the ticket at JR Kansai office. You need to plan well, as JR will print the ticket with the dates for the 5 days.
Also, the Wide Pass is inclusive of Shinkansen, manage to ride the Nozomi 700.
Since the pass is expensive, why not choose further distance to explore ? e.g. Himeji took 27 minutes using Shinkansen, while rapid train will take ~60+ minutes.
Next trip, then only stay in Osaka/Kyoto for shopping and don't wander out.
Kinosaki Onsen is the furthest, there is single train going direct without the need to change train or carry luggage around (e.g. Fukuchiyama). Check the timetable Kyoto-Kinosaki (3 trains per day) or Osaka-Kinosaki.
I would recommend going in a loop such as KIX - Kyoto (Nara) - Kinosaki direct - Himeji - Kobe - Osaka (day trip to Wakayama. Or you can even stay in Osaka and take day train to Himeji, Kobe & Wakayama for half-day, then come back to Osaka for shopping and meals in evening/night.
ICOCA you can imagine like HK Octopus or SG EZLink, can use in a lot of places, trains, convenience store, departmental store food stalls, restaurant, etc. So you don't get pocket full of 1/5/10 yen coins.

I will be staying in Osaka the entire trip and planning to go for daily trip for the above places for the exception of kinosaki since it's quite far from Osaka. I already have Suica, should i just buy icoca? i read tht suice is usable in kansai area.