I love me a Montana, but I'd go the custom 700 route. That way you can run whatever magazine/trigger guard set up you want. Obviously with the Kimber you're stuck to the blind mag and stuck with very limited stock options. The 700 offers you more choices to really hone in on what you want. End use also plays into consideration. Is this going to be a bench toy, walking varminter, etc.
I think if you're going to use longer bullets in the Montana you'll need to do some mag box, bolt stop, and possibly action opening work. I'm a big fan of the Montana blueprint but those issues would need to be considered.
Like GG mentioned, the 700/700 clone gives you a lot more options. I've done them bdl, adl, and M5 with a lot of different stocks and barrel contours. If there was a flush fit aics mag for the .223 I'd probably have all of them converted to M5.