In my last DnD session we had quite the kerfuffle with initiative. The problem was that we kept swapping in and out of combat time and then had to keep figuring out what initiative was again. This is a real issue with turn based combat, though normally you just navigate a single switch from simultaneous to turn based time and then you are good to go.
The situation was our party had opened a door into a room with several hidden enemies in it. We made our Perception roll to notice the hidden enemies and so combat began. Normally this would be fine - we fight, and either we die or they die.
But not this time! This time we cast Darkness, and our singular party member who can see through the darkness began shooting arrows at the enemies. The rest of us just hid as rushing out past the darkness into unknown foes seemed foolish. The enemies, not wanting to run into the darkness against unknown foes, just sat there. After a couple rounds of getting peppered with arrows one of the enemies had the bright idea of running up to the door that my group had opened and closing it.
So now combat isn't happening anymore. The two groups are back on either side of the door. The enemies wanted to ready actions to shoot us if they could see us, and we wanted to do the same. But both sides sitting there for extended periods readying actions doesn't work at all well. It makes for a very silly situation when finally somebody breaks the stalemate, that is for certain, and once you have had multiple rounds of everybody reading actions and nothing happening it feels like you have to break combat time.
But then what do you do to get back into combat time? Cancel all readied actions, for sure, then reroll initiative, I guess? But who goes first is a total mess, because nobody can do anything until somebody opens that door. And the person we wanted to open the door... do we just start at their initiative? Roll after the door opens? It is all a mess.
What ended up happening is quite beyond the basic rules. One of us opened the door, the other moved into their space simultaneous with the door opener moving back. Then the person moving forward grabbed an enemy and dragged them into the water in the room ahead of us. Our third person rushed into the room, I used my readied action to turn them into a giant crocodile, and the crocodile ate a dark elf. We broke at least three rules in that single turn.
And then we spent awhile rolling dice while a crocodile got stunned by a mind flayer but still kept that pesky dark elf in its jaws. And our monk had fun drowning a dark elf and then swimming away from a giant octopus. It was funny though - we spent half of our time in that fight passing turns, reading actions we knew wouldn't go off, and the other half actually doing fun stuff. It feels like we should police ourselves, somehow, and insist that nobody take powerful actions that lead us into stupid rules situations.
Normally I would yell about my solutions to this mess of swapping back and forth to combat time. But I just don't have one - it is an ugly consequence of turn based combat and I don't see a way out.