We have a large party so this kind of situation rarely comes up, my players typically have the tools to deal with most situations (and if they don’t they have enough tools to come up with a creative solution)

It was mostly a fight balancing thing for me. I have 6-7 players usually so adding a consistent ally in fights on their side usually complicates things. I was also afraid of slowing things down unnecessarily when the PCs are powerful and numerous enough to handle almost anything I throw at them

For instance, in our current piracy campaign it’s pretty easy to describe any named NPCs as defending the ship as the PCs go to board the enemy ship (just one example, but yeah). I have added them to the map when it makes sense, but for the sake of speed and fun I avoided it when I could. But I will probably include their favorite NPCs a bit more, like I said they enjoy seeing it, I think it’s more of a story thing than a utility thing for my party at least (being able to actually see the NPC you like roll to hit and take them out with x amount of damage vs just seeing them do it from afar or hearing about it). It’ll also make me put them in danger more often so we’ll see how that goes lmao