But, what if one player in the group wants to play out that toil? Perhaps he's playing some sort of religious type and wants to play out the penance of his character. I dunno. But, for whatever reason, Bob wants to play out that toil.
My geneal bias is to ask the group if it is OK to fast forwar before I, as the GM, do so. "Is it OK if we move forward to the next day?", for example, or "Is there anything else anyone wants to do in town?" Just as I would not allow a blanket "one no means skip it", I would not adopt a blanket "one yes means play it out". I would be more inclined to ask Bob's plans for playing this out, or what, specifically, he is actually wanting to play out. Presumably, Bob expects something of interest to happen which I have not considered. Could Bob's wish to play this out be overridden by the group as a whole? Sure.
What if the DM wants to introduce NPC's to the party during that toil? What if there are interesting encounters in that toil?
I return to my earlier statements about the desert. If, indeed, nothing of any note is goint to happen crossing the desert (or during the toil), then narrate it away. If the players want to, say, attempt to escape the toil, then they are deciding on actions taken by their characters, and that should generally be accepted.
I find all your questions do is highlight the fact that nothing is "always" and unilaterally assuming we should just skip a scene is seldom, if ever, appropriate.
Why is it okay for you to skip the toil, but, not the desert? What's the difference between the toil and the desert? After all, both are about equally relevant to the city.
Agreed - the group as a whole should decide whether we can skip the toil or the desert; no one player should be able to make that decision unilaterally. YAY - You win!
See, for me, I'd skip both, because in both cases, there is zero player buy in for either. But, why would you play through one and not the other?
See, I would skip both if there is both zero player interest and zero GM knowledge of anything relevant within. But we are back to me neither needing nor wanting a roadmap of the campaign events laid out before me as a player. I don't want that "management by committee" railroad either.