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I've never known a Jack and have never known anyone who named their son Jack, so I'm not sick of it. I don't think it's as popular in the U.S. as it has been in Britain. I think it's an okay name. The problem is I still think of it as a nickname for John, and as such, I don't like it as a full given name. The same goes with Molly, Eliza, and Jenny. It doesn't matter to me how long they've been used as names in their own right, if they started out as nicknames, they still seem too nicknamey to me. If I wanted a Jack, I'd name him John, and if I wanted an Eliza, I'd name her Elizabeth, etc.
The only person I've ever known who had two middle names was my mother-in-law. The only time I ever heard her make a comment about it, she seemed contemptuous of the idea, and seemed to think that it was pretentious. I think it's alright if that's what you want to do, but in a way it seems pointless, because most people would be more or less forced to drop the second one, since most forms, job applications, etc., only have room for one middle name or middle initial.