That's a valid point.
And honestly, I'm not worried about the loot he might get. It's the story telling aspect that bothers me. There must be some challenge, some drama, some cost, or what's the point? Isn't the whole point of bounded accuracy that even trivial challenges have some small chance of going sideways?
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I think very good responses have been given regarding this issue and the type of challenges a 12th level character should be facing which align with my own views on this topic. The thread looks long, so I may just be repeating what someone else said, and if that is the case I apologise.
My first response would be 'Why is the character wasting time on robbing sprees during downtime which are chump change? Why isn't he taking out crimelords and taking over their patch?'
Secondly, and I think my main reaction to the situation you are encountering with this rogue feature is - you don't need to rely on successful/failed rolls (or the potential for them) to create real drama. The situations themselves can create the drama and tension for you. Yes, you scout the mayor's house perfectly, effortlessly locating all the guards, judging their routines to perfection allowing you to slip inside undetected and make your way into the mayor's private office where you swiftly discover the cleverly hidden false bottom in one of his desk drawers that you unlocked with little effort. What you find inside horrifies you! Make a WISDOM saving throw.
Depending on the result of the WISDOM saving throw:
Fail: You are so struck by the horrors and the hideous secrets you have just learned that you do not react to the footsteps you hear coming down the hall. The door swings open - the mayor himself.
"What the hell! Who the ... how dare you! Guards! Intruder! He's trying to murder my daughter! Bring me his head!"
Success. YOu are so struck by the horrors and the hideous secrets you have just learned you react sluggishly to the footsteps you hear coming down the hall. You have just enough time to get over to the window and slide it up as the door swings open. The mayor himself. You are able to hide your face from view as he stutters.
"What the hell! Who the ... how dare you! Guards! Intruder! He's trying to murder my daughter! Bring me his head!"
Escape scene ensues. Hook to new grand adventure unlocked. More drama to follow as the real adventure begins. Trivial challenge gone sideways: yes, in a certain sense. There is a chance for that due to the WISDOM save (probably) a rogue weak spot, the possibility of being recognised by an influential member of the community, plus the rogue has learnt a very uncomfortable ruth that can create lots of story good tension in any number of ways in the future and now a new adventure path opens that the team will have to decide how they want to deal with which might be very contrary to their intentions, goals or desires.
So no tension was created as the rogue got in, rolls for stealth and lockpicking all irrelevant - result: you get to the good bits faster. And a new adventure begins. In that same situation, in all honesty, failing those rolls would just have been an obstacle to getting to the new adventure hook.
Thirdly, at level 12, when the rogue and his companions are dealing with 'the real adventure' and not the down time activities really the situations should reflect a much higher difficulty degree required for success right?
Trivial (DC 0) A task that is so easy that isn't worth a check. An adventurer can almost always succeed automatically.
Very Easy (DC 5) Requires a minimum level of competence or a bit of luck to accomplish.
Easy (DC 10) Requires a minimum level of competence or a bit of luck to accomplish.
Moderate (DC 15) Requires a bit more competence to accomplish. Can be completed more often than not by a character with both natural aptitude and specialized training.
Hard (DC 20) Include anything beyond the capabilities of the average person without aid or exceptional talent. Even with a bit of training and skill you still need some luck to pull it off (or maybe some specialized training).
Very Hard (DC 25) Achievable only by especially talented individuals. Nobody else should even bother trying.
Formidable (DC 30) Achievable only by the most trained, experienced, and talented individuals, and they probably still need help to pull it off.
Nearly Impossible (DC 35) An epic feat on which legendary tales are based on. The named masters of a skill come from acts such as these.
Godly (DC 40) Can't be done without assistance unless you're basically a demigod.
So at level 12, when they have got to the good stuff, surely the skill DCs include 'Very Hard (DC25)' and the odd 'Formiddable DC30' challenges in the mix as well, right? So those things you don't want to be so easily breezed through, should still have a chance of failure.
Lastly, I would advocate that the best traps (for example), the ones that create the most tension, are the traps that PCs are aware of but that require clever play and not just high rolls to deal with. SO in this case, the rogue can easily become aware of a trap and get a good read on relevant clues easily. But disarming the trap ... or getting past the trap ... that is going to require the players to absorb the information provided by the rogue to put their heads together and figure out how they want to proceed because how to disarm the trap is not immediately obvious. And even if the rogue could easily get past it, everyone else has to do the same too ... otherwise the rogue woud be all alone on the other side and having to deal with whatever is there waiting. SO even if the rogue can manage to largely remove any chance of their own failure getting past a trap, that doesn't mean that there is no tension. There is just a different kind of tension.
Anyway, hopefully that is helpful in some way.