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Trying to maximize any chances at Chicago and Columbia. Above a 4.0 and got a 169 in June then a 166 in July. Should I retake for the third time again Sept 8 and wait to apply in October (scoring would take a little while). Or apply with the 169 first week in September?

I know you haven't solicited advice re: NYU, but if you're targeting c and c, you should aim for the whole CCN. Be careful, and do your research on schools; when I applied, NYU took the average of all your LSATs. IDK if they've changed, or if C/C has a similar -- if unspoken-- policy.

Just focus on killing it when you RT. Practice in test conditions, and drill those LGs if you haven't already. If you haven't taken the famed computer virus problem, try doing that under stress. I've heard from Powerscore peeps that unconventional mapping games are forecasted to be on the rise.

What section are you doing the weakest in? If LG, definitely do whatever it takes to master them, then retake. 169 is in the range where literally every point matters.