"The goal is to create a single air cylinder lift mechanism that will also generate the rotation during the lift, similar to that of a click pen like in this YouTube video"
The cylinder you're thinking of has already been invented. The ones I've seen were small though... wouldn't deal with anything 15 foot diameter. So you buy a little one and see how it's made and then build one better suited for your application. I'm pretty sure they twist via a pin running in a groove. Google "twist clamp cylinder."