How much travel will you be doing within Kansai?
Were you thinking of using it to cover the trip to Nara and Kyoto? The airport bus is probably the most efficient way between ITM and Nara for ~ 1,500 yen. As mentioned, there's several fare options between Osaka and Kyoto so you don't need a pass for that leg.
https://www.okkbus.co.jp/en/timetable/T/#from
Kyoto tourist destinations are mostly served by bus or taxi and there's a 1 day tourist bus pass. Going by taxi in a group might be a good way to conserve energy given the summer heat and/or rain.
https://jprail.com/destinations/kans...jor-spots.html
Osaka has quite a few private lines similar to Tokyo metro vs JR. If you just plan on going within Osaka, you might be better served paying as you go with the IC Card fare. You can use a suica. Osaka subway + bus also offers 1 day pass if you'll be taking a lot of trips. Tennoji (random station as an estimate) to USJ is 190 yen.
https://jprail.com/travel-informatio...nsai-area.html
https://jprail.com/travel-informatio...jor-spots.html
https://jprail.com/travel-informatio...-in-osaka.html
I'd probably get a 7 day National pass and activate it on Day 2 or 6 given you're traveling as part of a group with 14 day pass. Day 2 activation gives you flexibility to ride the same train on the longer/expensive legs as your friends while people are still trying to get comfortable with transit. The Kansai Hiroshima pass + 1 way Smart-Ex ticket to Tokyo is a bit cheaper but 2,000 yen to have some flexibility, group solidarity (don't need to wonder if your pass coverage is different from theirs), and included reserved seats to Hiroshima is a decent trade off.
I'm a planner and usually do Japan solo but understand not all people are planners and groups require extra flexibility. I also pay out of pocket for in-city trips if non-JR is more direct, especially in the summer as I don't cope well with heat & humidity. If your travel mates (or you) like maximizing pass usage then check if you'd come out ahead with the pass for Mt. Fuji vs Kyoto.