I'm not really sure how a step pump or automatic pool cover pump will work in Massachusetts. I live just south of Worcester and by January, my pool is frozen solid about 6 inches or more thick and stays that way till St Patricks day. A cover pump or step pump would be frozen solid either sitting on the cover or on a step. If it were ont he top step, or on the cover, the pump would be encased in ice. Those automatic cover pumps do not work up here, at least thru the coldest part of the winter.
I lower the water level to just below the skimmer when i close. Sometime just before christmas, i'll check it and pull the water back down to around 15" below the top of the pool to get rid of any water level increase due to fall rains and early snow. I'ts usually not frozen solid at that point, but YMMV depending on how cold December is. After that, I dont do anything until about April.