After reading your post i kind of felt that i was on the right path with my first choices of both the vp9 and the vp9sk, and since reading it i may follow your lead in purchasing both. If for some reason you needed to choose one between the two for an EDC and wait awhile for the second, which would you have purchased first and why? Which is more versatile for you as a "first handgun "? Please bear in mind this would need to be considered as your first EDC.
You seem to be interested the most in the VP9, so as I mentioned above about a 22lr for training I just came upon this video check what he has to say about #2.
I myself have a S&W M&P 40/9 conversion and the full size M&P 22 both set up with Vortex Venom red dots.