So, this post is about a day old and I haven’t read everything after it, so apologies if you have already covered this, but I read this and had a thought I felt strongly about sharing.
It sounds like the way you run it, you take into account the amount of time spent on a task (let’s just roll with the lock picking example), set the DC accordingly, and abstract the whole process into one roll. Cool, I’m on board with you so far. When someone asks what happens when the player fails that check and asks to try again, you say that shouldn’t be possible, given that the amount of time being spend was already agreed upon, and immediately trying again would essentially mean they had spent more than the initial done on the task, which should have been accounted for in the one roll. You can’t just retroactively change how long you spent on the task. Ok, that makes sense.
My question is, what would you do if, instead of agreeing to spend a fixed amount of time on the task (let’s say a day, or something), the player said, “I want to keep trying until I get it. However long that takes”?