whitesand,
1. VS pump would be better because you have greater control of flow rate. Translates to lower cost.
2. Always 2" minimum. Gets better flow rates even for a small pool.
3. Separating drain and skimmer just allows more flow with the VS pump.
4. Best to use a 3 way valve on the suction side. No need to use shut off valves on the return side unless the equipment is below the water line. Might use a 3way valve for the deck jet.
Would suggest you add a auto-water filler for the pool.
Would also suggest a larger filter. Even though the pool is small it is better to have more filter capacity. It will extend the time between cleaning and no one complains about too much filtering capacity. 300 sq. ft. would my recommendation.
How about a pool cleaner? It's not on your list.
Not sure why you would need 2 skimmers. General rule is one per 500 sq. ft. of surface area.
Why 6 vacuum points?

Thanks for your help golfgeek!

I forget to add that there is a tree that is upwind of the pool. Would this make a difference?

I will take your recommendations to the PB and also ask for the justification for that many vacuum points.

The Vacuum points make sense if you are getting a Pool without a Main Drain... kinda the new thing that some PB's are starting...

Good Luck on the build...:-)