What I wouldn't want is to spend half a session getting to the castle, dealing with lame horses that throw shoes, wandering sheep and a dozen other completely unrelated side quests that are just the DM roadblocking.
But why are we assuming that anything whose relevance is not immediately obvious with crystal clarity to player and character alike is GM roadblocking. And why is the travel to the castle likely to be filled with lame horses throwing shoes and wandering sheep, etc. but all will become grand and wondrous once we get to the castle? I can certainly make you play out discussions with a neverending series of petty bureaucrats trying to get an audience with the Duke just as effectively as a lost sheep or lame horse.
If we want to assassinate the Duke and we happen to be in the wrong town, is it totally unreasonable to want the DM to redline travel to where the Duke is located?
The only reasonable answer to this question is "maybe". If the travel between the two towns is trivial, then it is completely reasonable. If it is not, then redlining it is unreasonable. Why shouldn't Lucas have redlined Obi-Wan and Luke going to Alderaan? Why did we need to role play the trip into Mos Eisley past the stormtroopers, the cantina scene to meet Han and Chewie, the takeoff of the Falcon, etc. And when we get there? What a @#(*# that GM is - he made up a planet destroying moon-sized battleship JUST TO SCREW THE PLAYERS OUT OF whatever the hell they wanted to do on Alderaan. WORST.GM.EVER!
How do you, the player, know whether the travel is, or is not, trivial? Answer: you don't. But you HAVE to be right, so every example of a non-trivial aspect to a scene you decided was in your way and should be skipped is dismissed as GM wankery, inserted retroactively to punish you for not playing his way.
One player wants to skip travel to the Duke's town. Another wants to skip interacting with that town's locals to learn the lay of the land. A third doesn't want to play out the trivialities of getting past the guards and castle defenses to the Duke himself, and a fourth is bored by tactical combat, so let's just skip the fight with the Duke. So here we are, 17 seconds after deciding we should ambush the Duke, standing over his bloody corpse. It seems like the entire assassination of the Duke was trivial! What shall we do next?
See, and that's where our styles diverge. To me, provoking Endurance checks is trivial and meaningless.
If a central theme of my character's cool is his vast endurance, then it ceases being trivial to me. The fact that he arrives fresh while the rest of you are exhausted and taking penalties shines a spotlight on my character's coolness. That has moved those ensurance checks from the realm of the trivial to the highlighting of Character Cool.
And, to turn your questions around, where does it stop? If we're introducing endurance checks, why not nature checks to avoid getting lost? What about wear and tear on vehicles? Do we roll checks to see if our mounts go lame? Animal handling checks to maintain the health of the animals? Etc.
Do they have significant consequences to the story? Do they allow a character his opportunity to show off his cool abilities and shine? If either is yes, then these are not trivial. If both are no, then why bother? But then, why bother making rolls to hit or damage? This is just trivia dragging out a combat scene. Let's get past that lame scene and move on to the interesting "escape from the Duke's vassals and avoid execution for assassinating the Duke" scene!
Why would I skip over everything in the castle getting to the Duke? That would be killing my enjoyment as well as everyone else's. That's counterproductive.
Because, for whatever reason, you don't find that aspect of the scenario likely to interest you. Your choice of what interests you or not is subjective, and seems pretty random from the outside. Why would the encounters in the castle to get to the Duke be so much more fascinating than the enounters on the road to get to the Duke's town, or the in town encounters to get to, and into, his castle?
At the end of the 5th Harry Potter book, his godfather is killed. Would it not be reasonable for his character to want revenge above all else? So why are we playing out YET ANOTHER YEAR at this setting wank school with no actual action involving the enemy? Don't waste my time interacting with this new teacher. Quit pushing her up the ranks every time we ignore her - haven't we made it clear we want to skip past that scene? I don't want to play out this "learn occlumency with Snape" crap. Snape's the enemy - end of story. Cut scene. Why the hell are we in that tower sifting through history AGAIN? Get to the action!
Your focus on advancing the store seems to me a great way to miss the story entirely.
I'm sorry, I don't care about setting. Setting, for me, is the least important consideration. So, given the choice of engaging in events unrelated to the assassination of the Duke plus assassinating the Duke, or going straight to the events related to assassinating the Duke, I'll always choose the latter.
While the desert, the road to the Duke and the spearcarriers are setting, so is City B, the Duke's castle and the Duke himself, and the Grell and the dungeon he occupies. The story does not take place in a vaccuum. You are simply choosing which elements of the setting you wish to explore and which you do not. If the GM tells you the Grell left, you will challenge that because the setting provided no reason for the creature to leave. It is the setting which provides a city in which you expect to find mercenaries you can hire. And, if you are travelling to the city where the Duke is located in order to assassinate him, whatever happens along the way is both part of the setting and events related to assassinating the Duke.
I'll give another example, this time when I was on the receiving end of someone ending a scene and moving things forward. We were playing the first module in the WOTC adventure path, Ashen Crown ((IIRC)) and we had captured a hobgoblin to get some information about the area we were in. My character interrogates the hobgoblin and rolls fantastically on his Intimidate check meaning that we're supposed to get some information out of this guy.
This goes back and forth for several minutes. One of the other players declares, "I kill the hobgoblin." in the middle of my sentence. I was taken a bit aback and, as an aside asked the player, "What the?" His response was, "The Dm was stonewalling and I'm tired of screwing around with this. Let's go."
At the time I was a bit put out but then I thought about it a bit and I realized that the other player was 100% right. The scene was over and I was likely beating a dead horse trying to get more information. By executing the hobgoblin, the player ended the scene and we got back to moving forward.
In this example, the scene was played out. "I can't be bothered to interact with the spearcarrier recruits, the desert or the trip to the Duke's town" does not play out the scene, but skips it. Making your example similar would be more on the lines of "I will question the Hobgoblin" folllowed immediately by "I kill the hobgoblin - he will have nothing of any interest to say and the GM will just stonewalll us". He has ended the scene before it could begin.
I don't really see a whole lot of difference between what he did and what I've done in the past.
I do, as you can see.
Not all RPG players are interested in simply "overcoming challenges" as the goal of play.
Feel free to describe an exciting, engaging game session that lacked any challenge to the players or characters. Until then, I believe that overcoming challenges is a large part of the game.
Because it's part of the setting and backstory? Because it provides colour?
If it has no impact whatsoever on the game - the story - they it provides no colour and is just useless description. If I can replace "desert" with "lake", "forest", " mountain", "plain" or "field of bones from an ancient battle", and the game will play out identically regardless of which one I pick, then it is useless, providing no value to any backstory and no coour to the game.
That wouldn't be a MacGuffin, then, would it? It's no longer a plot device, but a significant story element in itself.
Whether it is a significant story element depends on how it is used in the game. You can be lead to City B to accomplish any of the goals I mentioned without them being in any way significant to the story. Whether it is player-created is completely irrelevant to that determination.
I took that to be an implication of your remark upthread that a good player would RP his/her PC rather than pursue the mechanically advantageous option.
I would use "tactically advantageous option". A poor role player will always play a pawn. "Torch to the groin" gets the best questioning bonus? "Torch to the groin" it is. Who cares that I am a devout follower of the Lady of Mercy and Kindness and have sworn an oath to do no harm? That's just setting and backstorty crap. In BW, I believe I would simply say "my beliefs mean nothing - I want to get the answers, so Torch To The Groin!"
I personally prefer to focus on characters, and on situation - what's the conflict? what're the stakes? - than on setting as such.
You want to get past 200 miles of desert? I would say the conflict is "man versus nature". You want to get past the bandits in the desert, we have shifted to "man versus man". You have a morbid fear of sand? Now we're at "man versus himself". I don't know the stakes since no one remembers what's in City B to make it so important we cross the desert and get there.
I don't understand this idea that because you want to skip the boring stuff, you'd want to skip the good stuff too!
What I'm seeing is "I want to skip what I think will be boring before it has a chance to develop". After determining Hobgoblin has no useful information, it has become boring stuff. Killing it with no interaction is skipping what I think will be boring. And it seems like Hussar bounces between "I want to skip it because it bores me" and "I want to skip it because I expect something shinier beyond and I want that RIGHT NOW!"