AbdulAlhazred
Legend
Well, when we were in D/T or info gathering/free play we just had what we decided we needed. I'd tell the GM I was going down to the fighting pits to talk to my contact there about whatever. Of course I was armed, and might have noted having some other resources. If it devolved into major action, then I declared my loadout and that would carry over into the score. Sometimes the score just happened, like you say, but we always established initial position at that point.Then we have different experience. Now I've hoped that 5e would have more robust skill section with example DCs and stuff like that, but I have my own internal benchmarks for that stuff, so I manage. And the system seems quite sufficient for the way I run games. You can just treat most stuff via the fiction and roleplay, and then have some skill rolls when outcome is in doubt. Outside the combat mechanics what we basically have is very straightforward rules light vaguely simmish system, and that's basically what I have ever felt I truly need to run a RPG. Exploration, social situations, drama, emotions, setting of character goals, those really do not need rules most of the time.
Like what sort of concrete issues you have in mind?
We had a similar thing happen and the GM declared it was a score from that point on (even though we didn't roll engagement roll or do any usual pre-score stuff. But it was really short score and all characters did not even participate. And then we did all the after score stuff too. But it was weird and felt like a glitch in the system, though it was probably better that way as otherwise one character would have surely died. But I think the game should have answers to questions like "what gear you have in free play?" If things escalate into a sudden fight it sorta matters whether you have your weapons, armour, smoke bombs and other stuff with you or not!
I will say, we did quite a few split score loops where sometimes all three PCs were operating in different places doing different things. You can do that, just maintain position for each one.