Hunting rifle ammunition, which tends to be loaded a bit hotter, has the primer pockets enlarge after a few reloads, so I don't think it makes much difference which brand you choose. For this reason, when I reload for my .375 Ultra (Remington cases) I end up culling 3-5 cases per 100 each reloading session. The other calibers I load don't fare any better - although that would be expected if they are all loaded to similar pressures.
With regards to loading match ammo, Winchester cases have a reputation for being a bit more consistent in weight. The reason for this might be because they are lighter to start with, so if manufactured to the same tolerances as the other makers, they would have smaller case to case weight variation. That said, "out of the box" American brass does not seem to be as consistent as some of the European brass....but wouldn't it be nice if American brass had drilled flash holes?