I think my mistake was waiting too late (3 weeks before my flight) to buy tickets. Moreover, it also doesn't help that I'm insistent on "non-stop" flights and particular about the airline, aisle seat and flying days/times. I mean, sure I could easily save $100-150 on a flight to NY if I didn't mind a stop over, leaving mid-week or having to wake up at 4am to get to the airport for a 6am flight
But the inconvenience wouldn't be worth it to me.
I ended up paying about $480 for a flight to NY over the Labour Day long weekend, but at least I have $250-300 worth of airmile dollars to redeem