There are as many differing opinions of S&W values as the many models, barrel lengths and finishes produced. The value books are so general they are useless, IMO.
I've been buying and collecting S&W handguns for over forty years and I've seen may changes based on fleeting popularity and often hyped demand for different guns.
Factors that haven't been mentioned in this thread are issues like factory production numbers, region of the country, CC, target shooting or hunting use, unusual barrel lengths, urban or rural owners, politically driven issues like threatened ownership rights, and today the ever present fear we may have to protect our families our homes and our assets from the results of a collapsing economy. All these factors contribute to drive values up or down for different frame and barrel length guns.
As for the .357 vs the .44 mag issue -- publicity gleaned from films (Dirty Harry and Magnum Force), and gun writers (Elmer and Skeeter) have always been a major factor influencing what we want and what we eventually buy. It seems many of us are prone to buy what we believe everyone else wants or are told we should want.
I, like many others on this board have often stated the Mod 27 5" is my favorite S&W handgun. Why? For me it's because I love the P&R period 5" N frame, its finish, its balance, its look.
Would I chose something else as a favorite had they been available in the P&R period of production? Without a doubt! The same frame in a .41 or .44 mag 5" barrel length, which were only produced in numbers close to the finger count on both hands would have been the hottest selling S&W guns of all time, IMO, and the .41 would have been my first choice.... If you'd really like to see what desirability and scarcity can do to handgun values check those two rare N frame 5" guns out. I believe Doc 44 has the only 5" 41. A very elite few have the 5" 44's, and they ain't sellin'.....!!
Bottom line is to disregard what is "hot" or what "everyone else wants." Both the 44 and the 357 have a huge, well earned following and it is deserved. The "hot" guns and calibers of today will surely change tomorrow as they have so many times in the past...
JMHO