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So, I have just received a fairly prestigious award (can't say exactly what it is obviously). I am just wondering -- should I update the schools where I have apps pending now or wait for a possible waitlist in order to make a good LOCI.

Or does that depend on how much of a reach the school is? As in, if its a serious reach then update now because I'm likely to get a straight reject and if its a minor reach update later if I get waitlisted.

Just update now. Softs don't matter much at most schools, but if it's a fairly prestigious award, you should update the schools to make sure they evaluate your strongest application.

You can always come up with an excuse to send a LOCI later (or maybe even win another award).

Definitely update now.