.44 Special!
"With a .357, you get your choice of two more rounds than a similar size .44Spl, or a smaller overall gun if you go five-shot."
Well, I'm thinking that the 7-shot .357 magnums are made in "N-Frame"-sized guns, and that's a lot of extra weight you won't want to carry around just for 2 extra rounds. By contrast, a .44 Spec. can be had in either Smith's "L-frame"-sized gun (smaller) or Taurus's "K Frame"-sized gun. If that doesn't suit you, get one of the Charter Arms Bulldogs for a really small ("J frame") snubby.
"As to the "bigger hole" concept...what matters is the projectile width AFTER it expands! And that's a factor of bullet design and velocity."
So I guess you'd better do some praying that those 'lil .38 cal. pills will expand, regardless of getting plugged up with leather or any other cover-type obstruction.
But If expanding bullets are your cup of tea, the .45 ACP Hydra Shok expands at low velocity, so in theory it should be possible to obtain a .44 HP design that will do the same (my vote goes for Gold Dots).
Of course, if it doesn't expand, it's still pretty substantial at .44 caliber.
One more important factor also is the relative loudness of the two rounds - both are L-O-U-D out of a snubby, but the .357 takes the unpleasantness to a whole new plateau of discomfort.