Yeah, I didn't either until I needed to start jumping with students (working on instructor ratings).
At Mile-Hi on comp Velo, right? I'll bet you could get them all to go. I know there was some Cypres fire testing that went on independently with far less WL at about 2,000' (~sea level DZ with the Cypres set to fire higher). Article's in Skydiving Magazine and there are some comments on it somewhere in this site.
Totally. I'm thinking disorienting G-force related scenarios with smaller canopies where your AAD would get some much needed use after deployment, cutaway, etc, rather than in the initial freefall portion of the skydive.