Hi there!
Here are some routes and costs based on your listed travel:
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Kansai airport > Kyoto: ¥3,690 (75mins, 99km)
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Kyoto > Tokyo: ¥13,420 (161mins, 513km)
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Tokyo > Odawara: ¥3,840 (35mins, 83km)
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Odawara > Tokyo: ¥1,450 (36mins, 83km)
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Tokyo > Osaka: ¥13,950 (194mins, 556km)
JR ticket cost: ¥36,350 for 5 legs
Note that for Hakone the JR Pass will get you to Odawara, from where you should use the non-JR Odakyu lines to travel upto Hakone itself. I recommend the 2-day Hakone Free Pass which can be purchased on arrival into Odawara
A 7 day pass will certainly give you savings for your initial travel. The difference between a 7 and 14 day pass is ¥16,800, so you'll need to spend at least this much on further JR travel for a 14 day pass to be worthwhile. Looking at your travel, the only destination that I can think of that would fit your plans and cost this much would be a return trip to Hiroshima/Miyajima while you are in Osaka (normal cost of a return is around ¥20,000). If you were to add this trip on then a 14 day pass would become worthwhile I think.
You can look up precise train timetables and costs at the Hyperdia travel planning website and learn how to use Hyperdia for JR Pass holders through our video blog.
Hope this helps!