I remember reading in the past that Boeing said that 757's were expensive to make. They never built a bunch of them a month like they do with 737's so it never made sense to invest too much in production improvement.
If I remember right, 757's used to cost about double what a 737 did about 15-20 years ago.
I have a lot of time in that jet and it is my favorite. No one would pay that price for a jet when they can buy a 321 LR for 40 percent less. Yeah, the 321 LR is going to need more runway and will be stuck at 290 when heavy, but most of the routes for the 321 LR will have a bunch of runway on both ends.