I voted for the 375 even though my choice would be the 300 H&H but it wasn't on the list. Unless you are planning to hunt a lot of large bears, I would think the 300 would be your best bet. It will give you good long range performance with a good bulletlike the 180gr Scirocco II (the 200gr Accubond might be a good one too) and as you say can be loaded up with the 220s for big animals at closer range. I would also think the 300 Win would have better resale in the US than the 375.