For a guy on the fence between the Win-mag and the WSM, you've got to ask yourself one question. Does technology improve over 4 decades? If you have to think about it, just take a look at what you drive, or maybe the the computer/cell phone you are using to view this forum. Was it built in the 60s or 2000s? It would be hard to argue the 60s anything, is better, without some misconceptions. Sure, the 60s stuff has been around longer and is more known, but that don't make it better.
Is there some magic in hand loading a Win-mag, that makes is better? No, adding a little more gun powder, doesn't overcome the poor design of the casings tall, slender, design. The WSM makes more chamber pressure, with less gun powder. Why? Engineering. The WSMs wider design results in, a more instantaneous burn.