... purpose for the 5th screw? Was it merely another sideplate screw that was placed up by the hammer for sideplate retention, and later found unnecessary? What about the additional "bug screw" that was sometimes found up with the 5th screw?
When S&W introduced the J-frame in 1950 (what became the Chiefs Special) it was based on the older I-frame, except the frame and cylinder were larger to accommodate .38 S&W Special ammo.
The J-frame began as a 5-screw. The upper side plate screw was, yes, as you describe it for retention because the side plate was smooth all around the inside and needed that screw to hold it in place.
When S&W introduced the regular production Chiefs Special Airweight in October 1953 it was the first 4-screw J-frame, having lost the trigger guard screw. That was at serial number 24000 in the Chiefs Special series.
The upper side plate screw, although it had a large head, was a short, skinny screw, and repeated use would cause it to back out of the aluminum frame. That upper side plate screw is the bug screw. Dr. Jinks says the assemblers called it that because it was a bugger to install. To hold it in place S&W later added a small retainer screw.
Around Chiefs Special serial number 52600 in early 1955 S&W eliminated the need for the Chiefs Special Airweight's bug screw and its retainer screw by adding a tongue to the top of the side plate.
On December 13, 1955 the company issued Engineering Change #168 to "add a tongue to the top of all I, IT [Target Kit Guns], & J side plates, make the tongue the same as the JA38 [Chiefs Special Airweight] side plate. This will eliminate the bug screw (upper side plate screw) and counter bore and hole." The quote is from Dr. Jinks.
Obviously from Jack's earlier posts you can see the other frame sizes also followed the Chiefs Special Airweight's lead.