In my early 20's, I went through a couple of Blackhawks, a Super Blackhawk, a Redhawk, and a GP100, as well as a few S&W, Taurus, and Rossi revolvers. I never held on to anything very long though.
I sure wish that I had kept some of those nice revolvers that I owned back when I was younger. I've always regreted letting go of the GP100 and the Redhawk.
At 25 I inherited an old blued 3" S&W .32 S&W Long which I kept, at 27 I purchased a stainless 2" Rossi .38 Special which I kept, and at 41 I recently purchased a blued 4" 1979 Ruger Police Service Six .357 Magnum, and a blued 6.5" Heritage Rough Rider SA .22LR. I have a .22, a .32, a .38, and a .357 Magnum.
I like the .44 Magnums, but they seem like they're really "overkill" for target shooting and self defense. The .357 does so well in that role.