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I know that some people register and take the Feb or June LSAT again to see if scoring higher will get them off waitlists.

Is this a good approach? I don't get how LS admission keeps stringing applicants along. I mean, I guess no one really knows where they will end up until classes start. Even then, don't some schools notify acceptance to people?

It's like that hot girl/guy you always want to be with who makes you feel like there is a possibility, but always vague.

If it's enough to kick you over their median or higher, then yeah, the school would probably be happy to take you off the waitlist so long as they were seriously considering you. It certainly can't hurt.