I am among those who are drawn towards this bizarre Stooges short; certainly because of the reference to the "Penciltucky R.R. Co." (nyuk, nyuk, nyuk) and the railroad car named "Schmow," among others, plus this not being a "typical" Stooges entry. (And in this film in particular, Larry looks almost like a hippie version of former New York Mayor Ed Koch, especially when you consider the longer hair.)
But one has to wonder if this being judged among the worst of their offerings has as much to do with what was going on behind-the-scenes at Columbia's short-subjects department at the time this was being produced, as anything else in the film. This was from the period after Jules White became the sole producer/director of the Stooges (a situation, or 'soicumstance' if you will, which would stand until the closing of the short-subjects unit in 1958), following the firing of producer Hugh McCollum and the resignation of director Edward Bernds (all of whose directorial efforts of the Stooges were under McCollum) out of loyalty to his just-sacked boss and mentor. It is agreed among many Stooge-o-philes that the quality of their shorts plummeted mightily after White took full control. (To be sure, the Stooges' films weren't Shakespeare or anything else even slightly resembling "high art"; but for what they were, opinions differ among fans on when the quality decline took place - Curly's career-ending stroke and Shemp replacing him, the aforementioned backroom studio politics, etc.)
The question thus has to be asked (and probably unlikely to be answered, since almost all the participants are now dead, with the possible exception of actress Patricia Wright who played "Lenora"): How would the McCollum/Bernds duo have tackled such an unorthodox, offbeat script as this? Bernds is usually regarded by Stooge aficionados as helming some of their better entries, and especially his dealings with the actors and working around them (i.e. the final Curly shorts he crafted, where he took into account Curly's illness when making them, unlike White who merely shifted the action towards Moe and Larry; not to mention, in general, White's forcing everybody to work according to his idea of what "worked" in two-reel comedy).