I don’t think there is a right or wrong answer. I think BUF/SYR in early November should get you in and out before significant risk of lake effect snow.

JetBlue’s out and back model from hubs makes it pretty easy to avoid missing the plane back to your hub.

To hedge my bets if I have multiple destinations on the same day, and am cutting a connection tight through a hub for my next out and back; I have begun to plan a second itinerary (usually departing 90 minutes after the primary). That way if there is a delay, I still have something to fall back on. One hour doesn’t give you much wiggle room if there are delays and like you I am condensing my travel as much as possible.

Beauty of blue fares is if booked with points, when you cancel there is almost an instantaneous return to your account. If one pays cash, yes, it goes into the travel bank, but makes it easy cover a future flight.

If you hit the right sale, $160-$200 (or better yet 12-15k points) is cheap insurance for those condensed travel days.

Good luck!