ChrisLA, you guys will be fine up there.
I always stay with friends in Topanga Canyon when I'm in L.A., so I'm pretty familiar with Woodland Hills and Canoga Park. It's closer for groceries, take out and general shopping than Santa Monica and the Westside from there.
It's not bad at all around where you are going, and Westfield has made amazing upgrades and enhancements to the entire Topanga Plaza area. They continue to build new outdoor oriented phases on the surrounding parking lots. Warner Center is about to bulk up like crazy, which will only speed up the Orange Line conversion to LRT.
And you're absolutely right about Ventura Blvd. Just about everything you could possibly want or need can be found there. There are also incredible ethnic holes in the wall all over the place in little strip malls, jut like everywhere around town.
I'm guessing your largest adjustment will be Summer temps, but you'll adapt.
Once you guys get settled in, do yourselves a favor sometime and check out Sunday Brunch at the Sagebrush Cantina in Calabasas.