I put a Simms recoil pad on my .300 Winny and oh what a difference it made. It's simply unblievable that a recoil pad can do so much for taming the felt kick, but it does.
Before going on a trip to AK moose hunting 3 or 4 years ago, I shot my .300 win mag 120 shots at ranges out to 300 yards, and by the time the trip rolled around, I was very comfortable shooting it.
I plan on getting back upto AK for a another hunt in the next year or two, and I'll be using my .300 again.