I completely agree. 3 weeks to properly carbonate is an over-generalization. I agree, to think charles will be enjoying his first homebrew with the folks is pretty much out of the question, they may enjoy the spoils shortly after he leaves.
I always sample after a week, if for no better reason, because I can't wait. Most times it's a little flat, but I, like mixedbrewer, like to see it evolve. 2 weeks is usually more than enough time for carbonation. You may find, however, some beers will need time to.......... whatever. The fact that you mention using fruit, sometimes flavored beers take longer to, for a lack of a better term, mellow. Strong flavors fade, weak flavors emerge, etc. Some beers are what they are, most evolve over time.
That being said, I like and dislike your logic about transferring. The experience factor makes sense, but....... If it turns out badly, how do you know if the mistake was before or after the transfer? I would minimize the variables, and bottle the first. If it turns out good, which I'm sure it will, great. If not, you know that the problem was not transfer related. Make another of the same and transfer. Compare, learn. That's one of the great things about homebrewing.