I'm fine rolling with either philosophy, but I have NEVER enjoyed nor really gotten into raiding. The one raiding guild I rolled with basically just drug me along after all the nuts guys had everything anyway, so nobody else really needed anything. But as long as the rules are agreed to up front and there is a game mechanism for trading all the gear that drops I'd be fine with either roll on everything or roll to wear.
I will say that if I was designing the best system it would be roll on everything. Because many people abuse the roll to wear or roll to be polite/team player.
I guarantee you someone you thought wasn't abusing it was abusing it that you rolled with.
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Another word for expensive is successful.