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1). After using this wallet daily for something like 2.5 to 3.5 years I have not had a single card fall out of the wallet. The elastic holding the metal together secures the cards in place quite well, and even after years of use I can still put a single card in the wallet, turn it upside down and shake it and have it not fall out. With a larger amount of cards and constant shaking upside-down, the cards will gradually slide to about a 1/4th of the way exposed, but that is under very unrealistic conditions with elastic that isn't quiet as elasticy as it used to be (if it every becomes a problem, their website states they offer a lifetime warranty now).
2). I find the clip to be more aesthetically pleasing and durable. While I can not directly comment on the longevity of either as the clip has changed over the years, my money clip is like day one and I would imagine there are more issues you could run into with the elastic as time goes on unless you take great care of it. The one pro of the elastic that I could see is the potential of it being easier to get money into it.