I can't speak for the Gentoo community (though I have heard good things), but I've never seen sarcastic or elitist remarks at the Ubuntu forums.
Dumb questions, yes, but those generally can be avoided by not looking through the Absolute Beginners forum
I've not noticed that big of a lack of flexibility, but then again, I'm not really the type who likes to regularly build stuff from source and such.
I think most distros can offer more or less what you're aiming for. I wouldn't even be surprised if there's a security practice distro out there that has intentionally exploitable software in it. Distrowatch is a good site to check to look at the various available types that are out there.





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