To give it some perspective, Elmer Keith left off with the .44 special at 20 grains of 2400 with his 250 grain lswc. Lyman 49 lists 3 different lead bullets from 240 - 245 grains, with a max of 13.2 grains to stay under 14,000 CUP.
I currently load 20 grains of 2400 and a 245 grain lswc in .44 magnum.
So if you ask which would I rather have - .44 special or .357 mag and reloading doesn't come into play, I'd pick the .357 mag (as Tiro said, they are kept at low levels for older guns with weaker frames). If I can reload, .44 special.