yes, the higher cheek rise makes for a more comfortable fit. I tried lows with a cheapie 3-9x40 scope but did not like the recoil directly into my cheek. Mediums feel a lot better IMO with a 40mm scope.

I used to have a non thumbhole stock set up with a scope. Never had an uncomfortable feeling with it on the range. I think when a gun is naked at the store, they just seem odd until you throw a scope on and play with different mounts.