We're covering an awful lot of ground here, and at least with the suspension topic the whole "active" approach means different things between generations. Just to make sure: there is no air or ride height adjustability on the B8.5 (2013-2017) platform. If so-equipped on Q5 models, you can adjust the damping quality (firm...soft) via ADS. It's the B9 models that can be had with an air suspension that varies ride height.

Insurance. I moved from a three-year old 2013 Q5 into a new 2016 SQ5 and my insurance rates went up $6 every six months on the comprehensive coverage.

Ultimately, as much as I loved my Q5, I should've waited for the SQ. For me it was about buying the vehicle I really wanted, and minimizing the mod list and expense. That's "adult" me talking. As recent as 10 years ago I was a mod freak and lacked any type of forward vision in terms of return on investment. My point: drive 'em both. Supply shouldn't be an issue and with a bit of flexibility the market will offer plenty of examples of each type. See what works for you and checks off the appropriate items from your five senses.