I have owned high priiced Sauers, Sakos etc. All had Very nice classic custom checkering.
I also have owned Winchesters and Tiikas with average checkering and also Remingtons and Brownings with okay checkering.
In my opinion, "checkering attractive and have some utility" is the name of the game.
I personally like hand cut checkering because I use my guns for Moose, Deer, and Black Bear hunting in all types of weather, so I like some kind of texture.
If it was only Range shooting, I would prefer smooth Walnut stocks. My vote goes for "utility" checkering, but that suits my style of ownership.
I suppose its the old Frd/Chevy/Chrysler vs Audi, BMW, Volvo discussion?