Given the 4 hour difference between high tide at Squib and the start of the outgoing current at the Gut---I'd do both
There are still fish Down-Island at this time of the year. I remember when there was still a "real" rip at Wasque, going for an overnighter Veterans Day weekend and having a 31# along for the boat ride home. Which was the only one I could keep. Then getting some nice blues at South Cape.
My first choice to fish here, almost anytime of the year, is the backside of 4 major inlets, and the two that have inlet jetties. Then, out to the land of the Big Candle, then the North Fork. Those are a hike for me and I can usually find some quality fish closer to home. Less driving and much more solitude than Montauk.