Why? Like I get not liking the model, but your reasoning genuinely confuses me. The roll represents how well it goes overall. There is no infinite time scenario in a real game, so I refuse to discuss such a thing.
If there’s no infinite time scenario, then there’s a cost or consequence for failure, so repeated attempts should be allowed as long as the player is willing to pay the cost or risk the consequence.
If you go about the rest of your day, sleep, get your morning coffee and breakfast, and take another crack at it, I’d allow that, sure. But roll # 2 would be the only roll for that day, unless you can figure out a different way to go about the task.
Ok, so this is just establishing that each attempt “costs” one full day. As long as I’m willing and able to pay that cost, I should be allowed to do so as many times as I want.
And if you have 6 months of downtime, if I determine that there is a chance of you never getting it, it is perfectly valid for me to give you one roll to represent all your efforts during that downtime. I would generally break it into multiple rolls, but in general I always break complex tasks into multiple rolls. But the set of rolls I call for represent the sum total of your efforts within the available time, and that’s the only set of rolls using the stated approach.
Likewise, if one attempt “costs” 6 months of downtime and 6 months of downtime is what I have, great. I don’t take issue with this scenario, so long as it’s reasonable within the fiction (if it takes 6 months of downtime to try and find a buyer for my magic sword or something, that’s reasonable. If it takes 6 months of downtime to try and tie my shoe, not so much.)
There isn’t anything illogical or unreasonable about having a roll or set of rolls represent a certain amount of time trying. An attack roll isn’t a single sword stroke, and a stealth check isn’t a single step while hidden.
Not at all, and making each roll represent a certain amount of time trying is one of my go-to techniques for insuring actions have a cost or consequence for failure. Lots of things you might attempt while exploring a dungeon, for example, take 10 minutes to try in my game. Of course, if you fail you’re more than welcome to spend 10 more minutes and try again. But every time you do, we’re getting one step closer to a roll for random encounters, which I make once every hour during that time scale of exploration by default. Some actions, particularly those that are noisy or reckless, can cause additional rolls for random encounters as a cost or consequence for failure beyond that default.
Another approach might be to say that a task takes however much time it takes until something changes in the scenario - you can keep trying to pick that lock until you either get it or a monster wanders by and attacks you. In that case, getting interrupted by that wandering monster should be the cost for failure. But in
that case I should be allowed to go back to it after the monster is dealt with, as many times as I’m willing to risk that consequence on a failure.
What I take issue with isn’t rolls representing the total effort over a given period of time, or even over a nonspecific period of time if some consequence occurs before I finish on a failure. What I object to is being disallowed from making repeat attempts while I am still willing to pay the cost to try or risk the consequences of failure simply because the DM says “that was your best effort.”