The distance and ablity to end your trip before reaching your destination does get taken into account, but you are not wrong about leaving late to the catskills.
The problem is that the term "leaving late" is subjective. But based on your statement, it might be more OK to take a flight that lands in TLV 2 hours before shkia, versus driving up to the Catskills expecting to arrive 4 hours before Shkia, as there isn't much ability to terminate the trip while stuck in traffic in the middle of the highway.
Last time I came back from EY, it was a Friday LX flight which landed at JFK slightly after Chatzos. I only took it after asking my LOR whether I was allowed. There were plenty of frum Jews on the plane.
