1) Well the main advantage for the Outback is it's not a Jeep, plus Grand Cherokees I'd say are a bit more expensive. Looks like the Outback has .1" more ground clearance so that's a wash and the GC V6 has a little more power than the 3.6L Outback but the Outback gets better mpg. Honestly never looked into Grand Cherokees since my ex-GF's mom & grandparents had them in the 90s and they were always broken. I wouldn't mind a SRT-8 GC though.
2) All Outbacks (and all Subaru's minus the BRZ) have AWD but only the highest end Rav4 gets AWD, which I have no experience with but probably safe to say it's not as good as Subaru's. Could be talking out of my ass and maybe Toyota puts a symmetrical AWD system in their econo-crossover and not one that's FWD based. Rav4 will have a little more torque/hp than the 2.5L Outback but nowhere near the 3.6L engine. Outback also has slightly more ground clearance.
I'd really like to get a clear mid-00 Forester w/ the 2.5L turbo and swap some STi parts onto it.