Genie,
To me its not the number or restrictiveness of the rules but the quality of the musical experience that is the deciding factor.

Graham,
"The test is that he's a sucker and will put up with any crap to be around the "in-crowd", right?"

That's one valid way of looking at it.

But I see nothing wrong, per se, with following the rules of an "in-crowd". Sometimes the quality of a musical experience makes it worth the effort to put up with some crap, sometimes it doesn't. I can't claim to bat 1000, but I am not as quick as I once was to rule out participation purely on the basis of the crap.

"Toasted" was perhaps too strong a word. I tend to exaggerate for effect. But I've been on the receiving end of what was intended to be a "quiet word" and still felt toasted.

In my experience, it would be extremely unusual for a newbie to be handed a list of "restricted" songs or even simply told at the start what songs were off limits. That presupposes a degree of formal organization which is quite foreign to the sorts of small groups I think we are talking about. Part of the informality is that newcomers often/always learn things "the hard way" because there are no written rules.

Anyway,
These days, to me the issue isn't the number of rules, or their restrictiveness, or the ingroup/outgroup mentality. I'm sort of a bottom-liner here. If I feel that participation in the group is musically worth the effort, I'm willing to jump through some hoops. I'm just not as keen as I once was to have things done my way. I will occasionally submit and be assimilated and then exercise a subversive influence as a mole from within.

In my experience rules look very different depending upon your viewpoint. What looks like arbitrary ingroup crap to a newbie can "feel" right and make a certain sort of sense when you're a member.

The closest thing to the sort of musical freedom some of the participants in this thread seem to yearn for is found doing music with friends I've known and played with for years/decades. They'll put up with almost anything. They'll still whine though.