Crispy crust is mostly achieved (from my experience) by making the dough slightly thinner than the rest of the pizza around the edges. I've personally only used the window pane test a couple of times with mostly positive results. It's certainly a good judgment tool and you should be fine using it, but remember to not make the edges too thin. We want crispy, not burnt and crumbling to pieces after all!
As for the olive oil, I would strongly suggest coating the dough in it before kneading. I would use just enough to coat it though, it will make the dough easier to handle and locks in much needed moisture.