Ah, yeah. I can see the analogy. I definitely understand the problem of "doing everything all over again" and I can see what you mean. But the reason I said this wasn't only because of Hatsukoi 1/1. I remember him not liking Tsujidou. I hope the same thing doesn't happen with HoshiOri. I know it's a project they wanted to do from the beginning, and I hope that passion they have for it holds them together for at least that one VN they wanted to do all along. Also, I am afraid of HoshiOri's length. Only few can survive projects on VNs of such length. That's why I am hoping they'll have the will, love, and energy to see it through the end.
Err... I never feel empty when I finish things I like XD You may be right, though. I don't know Trip personally, so he may very well be one of those people who feel empty after they finish doing something they like.