I've got a deal going on my fifth Kimber, so its safe to say that I like them.
Winchester has cranked out decades worth of "so-so" Model 70s. That seems to have changed when production was moved (resumed) to the FN plant. I've got 4 of the new ones, a Feather-weight in .270 with wood upgrade, a Cabelas sSupergrade featherweight in .270, a .375 Alaskan and a .458 Safari. I'll put the workmanship, design, function and accuracy for type up against anything remotely close in price.
Kimbers can be a little picky about the loads because of the paper thin barrel. That sort of goes with the territory. Many of them seem to have the mag box pinched between the action and floor-plate. Some I had to work a little harder to find a load than others but I got there on all of them. Triggers are better than many aftermarket ones, and rifles come pillar bedded. Design is great, but why wouldn't it be? They copied a M70.
There's not much to say about the M70s except that they got rid of that 2 piece 3 screw action bending abortion of bottom metal and generally got their shyte together on quality control. Its about time. The trigger is changed, some will miss the total simplicity of the old one and some will notice that the new one has a nicer pull. They tend to be a little heavy in the pull, a spring swap fixes that.
What you pick will depend more on what you want than anything. If you want a standard weight hunting rifle look at the Winchester. If you want to shave some weight and know what you're getting into grab a Kimber. If you want a target rifle, don't buy either.