I don't have your exact situation, but I'll leave my thoughts.
I have a M40 F2.8, M50 F1.7, and a Sigma 50 F1.4 (HSM). I got the M50 first, and I used it a little on my k-x, but not so much after. I got my Sigma 50 F1.4 second (well, after a few other things), and now that is my favorite lens. The F1.4 is just purely fantastic for what I shoot (pics of my girlfriend, food indoors, pics of my girlfriend indoors, etc). I don't even mind the size - surely the bigger the lens, the manlier I am.
Then I got the M40 F2.8, and I
really love the size. I dislike the manual focus on my k-x, but its size was just great. I think - if I had a k-01 or if I had the DA 40 Ltd, then I would use it for my street photography. My Sigma 50 would be relegated to more serious events (pics of my girlfriend). So it's not so much the focal length between 50mm and 40mm, but the sheer design of the two lenses.
Also - as far as sharp wide open goes - my Sigma 50:
http://farm9.staticflickr.com/8315/8037491972_fa1e425e92_o.jpg <-full size
It's good enough, especially if you aren't going full size. With some sharpening and post processing, the DA*55 is plenty useful at 1.4.