I have something of a love/hate relationship with the .44 Special. On the one hand, I really want to like the cartridge as I enjoy the history of it and I think it has a lot of potential. On the other hand, I've never been able to find a gun or non-boutique factory loading for it that couldn't be substituted with something else which would accomplish the same goals as well or better.
The primary problem that I see with the .44 Special is the low-pressures to which it is loaded. Much like the standard pressure .38 Special, the .44 Special in SAAMI compliant loadings has a difficult time attaining high enough velocities from a short-to-medium length barrel to reliably expand a JHP bullet without the need for a very light and/or fragile bullet which may not penetrate particularly well.
Now, obviously a handloader can address these shortcomings as data is out there ranging from mild factory-equivalent loads to "honest" .44 Special loads like that developed by Skeeter Skelton to low-end .44 Magnum level loads like those of Elmer Kieth. However, even the Skelton-level loads require a large-frame revolver like a S&W N-Frame to handle a steady diet of them. While a large frame .44 Special revolver loaded with Skelton-level ammunition would be a formidable weapon, for roughly the same size and weight one could have the revolver chambered for .44 Magnum and add another level of versatility to the gun.
The smaller guns in which I feel the .44 Special would be most useful, on the other hand, aren't particularly well suited to ammunition beyond standard factory loadings which is what hampers the cartridge in the first place. The Charter Arms Bulldog is well known for not being tolerant of hot-loaded .44 Special ammunition and I wouldn't trust the small, five-shot Taurus and Rossi .44's much further. Even the S&W L-Frames like the 696, arguably the best of the "small" .44 Specials, are limited by a very thin forcing cone which is known to crack when fired with too much hot ammunition.
I have tried to scratch the .44 Special itch on two separate occasions and, in both cases, I was never completely satisfied. The first try was with a Taurus 445 snub. While it looked like a great carry gun at the time, I found that the rather smallish grips made shooting anything more than mild cowboy action loads painful due to the vicious muzzle flip of such a heavy bullet from a 2" barrel. While I could have fitted a set of larger, more comfortable grips, that would have defeated the entire purpose of the revolver: a compact CCW gun. I eventually sold it and put the money towards my 2 1/2" S&W M66-2 and have never regretted the decision.
The second .44 Special that I owned was a beautiful S&W M21-4 in nickel. While that gun was much more pleasant to shoot and I liked it much more than the Taurus, it still eventually proved to have its shortcomings. First, the fixed sights were regulated not for the standard weight of 246gr, but rather for 200gr bullets. While this meant that the POI was dead on with most JHP loadings, heavier 240-246gr LRN practice ammo and my previously worked up handloads with 245gr SWC's shot unacceptably high at 25-30 yards. Also, due to its tapered barrel, it was relatively light for an N-Frame at 37.5oz. While not quite light enough to be appreciably easier to carry than other N-Frames, it did make the recoil with hotter handloads rather unpleasant (I'd envisioned it as sort of a light Magnum). While I really, really wanted to like the gun and kept it much longer than the Taurus, I eventually sold it in order to finance the purchase of a 4" S&W 629. Looking back, if I'd been able to afford it, I wish I'd have kept the M21 and bought the 629 outright (particularly since I later learned that only about 600 M21-4's had been made with the nickel finish).
So, for practical purposes, I've finally pretty much written off the .44 Special. When it comes to a working gun, make mine a Magnum. That being said, part of me still yearns for a .44 Special even if only for an interesting addition to my collection (perhaps accumulation would be a better word). Unfortunately, most of the .44 Special guns I've come across since selling my M21 have been either of lesser quality than what I'd like or priced too high for me to justify to myself. Within the last month a local shop had a 3" Lew Horton S&W 624 that I'd have bought if not for the $900 price tag and just today I was tempted by a pristine 696 at another local shop, but I couldn't justify the near $800 price tag. In the mean time, I continue to accumulate .357 Magnums (I'm currently up to four) and I've never sold one yet. Oh well, perhaps one day I'll find just the right .44 Special and end my internal conflict.