E38 all the way if you like to drive. If you like to be be driven, W140. In the long run, bmw maintenance will be cheaper and more predictable. MB is like driving a ticking time bomb. Im sure you are already aware of 140 horror stories. E38 radiator and cats tend to go out at around 70-80k, but MB has the same problems AND more. W140s gadgets are bound to go bad sooner or later and MB parts cost a fortune. If youre a hands on kinda guy, maintenance wont be too expensive. I drive a 530, but the lux factor doesnt measure up to its bigger brother. 7 cabin space makes 5 feel like an econobox. I love the rear leg room. I dont know how BMW could have gone from that classic design to current e65.