I would choose (and have chosen several times), the 300 Win over the 300 Wby mainly because I don't like to fuss with the long freebore of the Wby. Sometimes a rifle likes to have the bullet close to the lands, and with the Wby that just isn't an option in a SAAMI spec chamber.
That's primarily why I'm having my .300 Wby Sako 75 rebarreled to .300 Win with a Lilja barrel. I can play around with seating depth, but with so much freebore in the Wby. it doesn't seem to matter since I can't get close to the lands. Plus, I can get my favorite Lapua brass in .300 Win but not .300 Wby.
