Matt, I went through the same thought process a couple of years ago. I considered whether the added cost of the 441 was justified and decided for me, it wasn't. I'm not sure I understand your calculations, but I have a 440 in the attic of my shop (intake on the cyclone is a good 17' above the shop floor) and a far less than ideal ductwork layout, which includes a couple (sometimes three) 90 degree bends for most tools and and a "T" fitting at the ceiling where two runs meet and go through into the attic. Awful from a design standpoint, but it really makes little difference. The 440 is more than powerful enough to overcome my design compromises. That being said it is hard to say how analogous my situation may be to yours. Don't know if this really helps, but figured I would offer it anyway.