IMHO the biggest issue with Steven's approach to TWGOK is the way it's being lumped together with Yosuga no Sora. He finds a custom excuse to dismiss it later ("insults intelligence"), but the structure of the post makes me suspect that its destiny was sealed beforehand. Note that at no point Steven implied that TWGOK was an eroge adaptation, which it indeed is not, but the progression...
Even if it were, it could be fine. Generally I had good luck with eroge adaptations. The ef ~melo~ was perhaps the best Shinbo thing I ever watched (45 posts in category!). To Heart is an undying classic. Sure, Yoakena was let down by poor writing, but Feena left a deep impression. The secret here is to avoid drek like Yosuga no Sora. It's not like it's hard to know what it what.
Getting back to TWGOK, I heard it was quite nice. Jessi's fits only add to the flavour, she hates all good shows. I used to catalogue her grotesque reactions at Ani-nouto before getting bored of them. My only problem with TWGOK is that the manga is ongoing, so we're not getting a decent ending.
It may yet transpire that I open TWGOK and it turns sour right away, but at least I give it a chance, eroge tropes or not.
UPDATE: Chris reminds about the "monster of the week" nature of TWGOK.