I wonder if anything has changed over the last 11 years for anyone?
Nothing has changed over the last
51 years.
The problem I have with "one and one" is it doesn't make any sense.
There is hardly anything RAW that makes sense after a large enough amount of scrutiny and reality checks. A game rule is supposed to be usable, not perfect, and realistic only up to a certain level, but as players keep looking purposefully at counter-examples to prove their point, no level is realistic enough for them.
My front door warps a bit with the weather. This means sometimes I try to open it, and it sticks, forcing me to try a few times. Imagine if I lived in a "one and done" world! I'd be calling a locksmith every time I tried to open my door and failed!
What benefits to a game would rolling multiple times bring in such a case? Do you want a chance that you have to call the locksmith? If yes, then roll, once, with numbers chosen so that more or less the probability of failure suits your expectations. If no, don't roll, just
narrate that this time you had to try many times.
I like the old 3E style approach in this regard. If you are not under duress and there are not dangerous consequences of note, you can "take 10", so the outcome of your roll is 10. If you have lots of time, and no consequences for failure, then you can "take 20", so the outcome of your roll is 20, but the cost is that you take 20x the time to do the action very carefully. In the case of say picking a lock, taking 20 may not be permissible if the lock could jam, or if your lockpicks could break. Up to the DM, if you can take 10 or 20 in a given situation.
I do not fully endorse "Take 10" or "passive skills" rules, they have the byproduct of making it not possible to do your best, and there are plenty of complications due to how different skills can work in different circumstances, so to me these rules don't improve the game but only complicate it with unnecessary discussions. The original 3e "Take 20" rule was more solid, as is something like "Reliable Talent" which sets a minimum default
after rolling.
In general, I would be inclined to be lenient and allow characters to retry if they fail, but there could be consequences of intermediate failures.
Maybe a usable compromise could be, that retries are possible but there
will be a cost for failure. But this has to be a real cost, not a potential cost that maybe it won't matter at all. This is why I am skeptic of house rules on adding more time spent to each attempts, because sometimes times matters and some other times it really doesn't.
Ok, but a part of my point is that the ability to perform a task as a bonus action should imply that it takes a very short amount of time to make the check, even outside of combat, right? So if, as in the original post (so long, long ago), the DM wants to say "ok, the check takes 1 minute, a retry takes 5 minutes" and so on, what does that mean for a Thief?
Because it doesn't really make sense that a Thief can do something in combat along with a normal action and movement inside of 6 seconds, but out of combat, suddenly it takes 10x that amount of time or longer.
The fault is allowing the Thief to do something unreasonable in combat in the first place. But apparently we want the game to be both realistic and unrealistic in the same time, because out of combat we want the "lord of the rings" feeling of taking ages to do everything, and in combat we want the "mission impossible" feeling of doing many over the top stuff at once. The idea that a PC can disarm a trap or pick a lock in one turn during combat is because players want a WOW! factor, but then some interprete this as a sort of "law of nature" that to disarm a trap always takes 6 seconds by default in the world.
If you want more consistency, you can make different decisions depending on how complex the challenge is:
a) the trap/lock can be handled with a combat action and a dice roll (because under pressure), while out of combat success is automatic
b) the trap/lock cannot be handled under pressure (automatic failure), and required a dice roll out of combat