I can't think of why there isn't more discussion about Yume kara, Samenai, barring an aesthetic bias when talking about history. The first work produced by Studio Shaft, nearly a decade after their founding as a studio and a decade before their next work, would be hard to recognize without anyone saying it—no Shaft aesthetic style, no quirky writing, not even the small idiosyncrasies you would find in their other early works like Moon Phase and .Koni-chan—but it marks the birth of their production work nevertheless. On the flip side it deals with the awkward topic of high schoolers doing porn, and even though the packaging and resolution are bland as can be I'd imagine it would at least make it to the discussion table as some sort of “figure A”.
Maybe there's just too much of that packaging. All but the last fifth of the 35-minute runtime is the usual boy-meets-girl, boys-friends-tease-boy, girls-friends-tease-boy, and the like. A dating montage towards the middle, set to a Ryouko Sano insert, basically tells you everything you need to know about the burgeoning couple, save for the gossip at the start about the girl Sao having starred in a porno, which seems to only cause her future boyfriend Takao to be slightly more hesitant in making a move (although that might just be the usual awkwardness that drives girls nuts). One day Sao runs out during a test, and Takao tries to comfort her, leading her to invite him to understand her feelings and anxieties by starring with her in the next video.
For what it's worth, I'd love to live in a world where high school anxieties are cured by shooting porn with your friends and where the production company is a-ok with stars bringing newbies in as their partners. But having committed to such a fantasy world, the choice for Takao to reject Sao's work, and Sao to come to her senses as soon as Takao gives her a place to be outside of porn, is a little bit disgusting. There are reasons to leave on a dime, from abuse to not needing the money anymore, but the idea of him solving all her dependency issues mid strip tease is a pretty terrible reason. Another interesting note: the whole way the scene is conducted it feels like there's no transaction going on, no money or responsibilities. We're made to feel like she's only doing this to find a place, as if any other financial or pleasure motivations would ruin the purity of her character, and of course ruin the payoff of Takao whisking her away.
I don't buy it for a second. Yume kara, Samenai is certainly a reflection of where Shaft had to mature from. Of course looking at Araragi in Nisemonogatari one might imagine they didn't grow up at all, but I would argue otherwise. Besides maturing in terms of visuals past the incredibly bland design of Yume kara, Samenai and developing a unique style of pacing rather than twiddling their thumbs for 25 minutes, the Shaft of today goes out on a limb to be creepy and provocative only to smack themselves in the face for it, roping us in while also chewing themselves out for being weird nerds. There isn't an ounce of self-awareness here, even when they're playing with fire. You can argue their morals and actual substantive content are still on shaky ground, but to my mind there was nowhere to go but up.