Ready Action and "combat"

[Hecuba]

Something for nothing? You guess/deduce something and if you are right you are rewarded, nothing cheesy here.

I'm not sure I agree with your assessment of how cheesy that wold be (I've had a couple characters players players who are real characters and seem to expect to be able to use something like this to get a super-duper second surprise), but if you are going to reward a character in that situation the reward should be structured around the surprise mechanic. That's what its for.

What you are discussing seems to me to be, approximately, giving a character something like the alert feat because the player can meta-game well.

I don't care about initiative order when you are haggling. That's my whole point. There IS no initiative order, but there MAY be situations where someone is waiting for something to happen. I'm saying it's ridiculous that within combat you can always choose to act before some event if it hasn't happened yet, whereas out of combat, if you take the stance that "ready actions are only for combat", you can't. "The rules that best fit to adjudicate" change substantially whether or not someone is trying to kill you. That's bad.

Initiative is not combat-only: that's why "other fast-paced situations" are noted. If the exact order of events and interactions are important, that's what initiative is for.
If you're in the more abstracted narrative time-frame instead, then its deliberately abstract and narrative. That's is a feature, not a bug: trying to bypass it blurs a the specifically designed pathway for moving between narrative and tactical time (initiative).

That shouldn't mean you can't prepare for things mechanically - it just means you adjudicate the preparation in a way that is less dependent on the exact order of turns. If you're waiting for the exact right time to interject when your teammate is haggling, or waiting to time an attempt to be sneaky for the exact time your party member provides a distraction, or what have you then the mechanic result should be advantage from the help mechanic. If you've noticed the thugs eyeing you and spoiling for a fight, the mechanical benefit of preparation for the fight should be a change in how surprise is adjudicated.

As best I can tell, the complaints in the thread amount to:

• My DM never enters initiative except for combat
  
  • Well, that sucks. It's called out for use in other fast paced situations where order of events matters. Consider talking to them about the subject.
• My DM won't let me prepare for events outside of initiative in any way with mechanical consequence because the ready action is tied to initiative.
  
  • Well, that sucks. If the situation is at all cooperative, consider reminding them of the mechanics for helping on checks and group checks. Otherwise, consider talking to them about their willingness to hand out advantage/disadvantage.
• My DM won't let me prepare for combat that is clearly about to start.
  
  • Well, that sucks. Consider discussing with them what their threshold for adjudicating surprise is.
• My DM won't let me use the ready action to influence the exact order of events outside initiative.
  
  • Well, yeah. The adjudicating the exact order of events is what initiative is for: if you're not in initiative, that's a signal that you're working in a narrative frame where such matters are abstracted.
    If you're chafing under this consider whether you're currently taking advantage of other ways to benefit from preparation outside of initiative and/or talk to your DM about more liberal use of initiative outside combat.