You wind up in hilly woodlands as you leave the coastal plains of each station location,that's why the "toss up" between GY and MY.
The Land of Enchantment is not Flyover country!
I have to respectfully disagree on both GY and MY. I've been fortunate to work at both locations, especially at Montauk. Montauk does have some significant terrain as you approach the last crossing, but it's much farther than what you see in the second picture. Also, if you look at pictures dating back to pre-WW II, just about all of the hills there were bare, save scrub oak and brush. Poke through Arrt's archives regarding Montauk, especially during the Camp Wikoff period, and you'll see the hills are both farther away and bare. Also the early Montauk stations were closer to the water, not far from Fort Pond Bay, so that would be more apparent in the second pic. Greenport is a nearly flat grade into the village.
I'd go with K&K and say Richmond Hill. I've also frequented that station up to about 2011 and would ride a CE out there to get Alfie's (pizza) or Jahn's, and catch it on the way back from Pond. I've often wondered what it was like prior to elevation, and that second pic may be it. Right as the ROW hits Forest Park, there's a big ridge and you have quite a few steep grades going from there to Maspeth. Must have been fun firing that prior to elevation with a steam engine.
