From thoughts on grinding, event triggers, sensei quest etc...
Selebus knows everyone, who went beyond room with clocks are just using wiki, guide, urm to bypass the grind. So about making player feel the uncomfortable loneliness sensei feels, i don't think sel was going for that.
Sel is a "Turkish Ice Cream Man". You pay for ice cream and he gives you the ice cream. But it's not so easy because he uses different tricks to confuse you so you can't just grab it. You have to work for it. It is part of the experience.
And Sel is an amazing ice cream maker, but the problem is he is talentless on all the other aspects. he doesn't have the sleight of hands to to make confusing tricks that outsmart you so that you can't grab the ice cream. So what does he do? He just put the ice cream on the stick and put it on the air where you cant reach it and swinging it. Sure you can't grab it just like the other Turkish Ice Cream vendors but it just isn't the same. You just wait there checking your phone while waiting for selebus arms to tire out and had to put it down.(This is the metaphor for urm, guide etc...)
Sure there was an attempt but neither side was involved in this experience.
He knows how off putting it all is, but still does it. And he can partly get away with it because he knows his turkish ice cream is much better than those italian ice cream or brand cornettos. Sure his product have terrible wrappers, soft and wet cones, his vendor smells like shit. But he has the best ice cream around here. And he enjoys this.
TLDR:
He is the kid who proudly says "i didn't study at all but still got the A- on math test." But he is trying to be a mechanical engineer.
Or Sel is a talented writer but a talentless artist, because his art is a sandbox game not a book or visual novel.