Is there any possibility of gaining elevation without being on the edge of a cliff? In other words, topography that just gains elevation overall, rather than in certain peaks. For example, 9W just outside New York City is a gently climb heading north from the George Washington Bridge (very gently - 300 ft over 8 miles) - this is in comparison to riding along the river about 1/2 mile to the east, which is nearly flat along the water line for about 7 miles before shooting up 450 ft in the last mile to meet the main road.
Something like 9W might help you climb a little bit while you figure out how to best tackle the situation.