Between the WOC and Summer Flap, I'd pick the SF. That one's an easy choice for me because I never liked the concept of a wallet on a chain. I'm in my 30's, and the WOC seems too teenager-ish for me. Of course, there're a lot of tPFers that totally rock the WOC, so I think it just depends on your age and style.
It's a harder choice between the jumbo and the SF. Utimately, I think that the jumbo is too much in patent fushia. I sometimes think that I should have gotten the fushia ML when I had the chance, but for the $1,500 price tag of the SF, I can't really say that I regret getting the SF. For the price, I can afford to have the fushia as a fun seasonal color and won't feel wasteful when I'm over it.