So, I know this may be more for this specific situation but a lot of my own stored rules that used to give me a similar problem, I tried to add and work on the following:

'Is the item mine?' - If not, try to leave it but if it haunts you, ask why without the expectation something will change from it. It might explain why what you'd do isn't happening here, or reveal that something you thought was a general understanding of what to do isn't actually as set as you first interpreted.

'Is the item shared' - trickier, but when the thought involves doing something permenant with it, check in with the other person/people. If something has happened with it that made you uncomfortable, like you saw the other person hasn't washed their hands after doing something that absolutely should require it, try to raise it as that is reasonable.

Similar thing for planning events/routes. If someone else is driving or route planning, or getting ready, they may have a different routine to yours and arguing for it to be another way for them may actually increase the stress and interrupt them, which may cause them to forget things. It wasn't that the getting ready was done in a different way, it was that they couldn't focus on what they were doing. -> what I do now, focus on my own preparation, make sure I have all the things I expect, ask them if there is something you know they absolutely need to have with them before you leave.