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KarinsDad, I've noticed you don't like extensive up-front rolling, which seems contradictory to your professed dislike of time-wasting on multiple posts.
If by "up front rolling" you mean "player deciding to roll skills out of the blue", then you are correct that I do not prefer it.
I think actual up front rolling is a good idea. As an example, when 4M asked for 3 skill rolls from each of the PCs at the start of this adventure segment.
But, there is a difference between up front rolling and the players deciding when their skills are applicable as opposed to the DM deciding it. By having the player decide when to roll the dice, it strongly influences the DM to handle the situation based on the results of the dice where the DM might not want to do so. The DM might not have wanted a roll. He might have wanted to just roleplay a situation, or he might want more details from the players before deciding how to handle a given situation.
I'll give you an example (which happened here on PBP a few years back, a game 4M and Neurotic was in). A player rolled an unasked for Diplomacy roll while treating an NPC like total crap. As DM, I didn't ask for a Diplomacy roll. The player rolled a natural 20, so he expected that the NPC would be fawning and such. Based on his roleplaying, I had the NPC become suspicious. Then, another player rolled a critical Bluff and it moved the man from suspicious to interested. But, the first player saw 2 critical dice rolls, the NPC not acting like he thought he should, and quit the game because he was not having fun. All because he rolled dice first instead of roleplaying first, and he was used to games where the dice dictated the outcome of events.
Another example, the DM describes an alleyway. Instead of the players describing what they are trying to accomplish and the DM responding, one player decides to search and roll Perception dice. The alleyway is lengthy with multiple (let's say 3) possible things to find. The DM knows of the multiple potential finds, but the player does not. If the player throws out an unasked for skill roll, which thing does the DM decide to use that roll for? The first, the second, or the third?
Say that there is a trap on the ground. The DM determines that the PCs cannot just find it accidentally without setting it off, that they have to actively search the ground.
But by having the player decide to roll the dice, say he rolls great, then we can get into a situation where the DM decides that (as you expressed it) it was logical that the PC was going to search the door and not the ground, but the player is wondering why his great Perception roll didn't notice the trap on the ground.
Do we use that same great Perception roll all of the way down the alleyway until something is found with that single roll?
The players do not know all of the details of the situation and environment. The DM does. So, the DM should be asking for skill rolls based on what the players want to do. Maybe 4M did NOT think that stealth was applicable for you. Maybe he didn't care how loud the PC was, he cared if the PC was perceptive enough to find the NPCs.
A skill challenge is a different beast. The DM is stating up front that he wants skill rolls (note: 4M talked about a skill challenge after you decided to roll a skill). So if a player attempts a skill in a skill challenge that the DM does not think applicable, then the DM can just say so, regardless of whether the player rolled ahead of time or not. There is an expectation that the players will be taking turns rolls skills in a skill challenge.
A combat encounter is a different beast. There is an expectation that the players will be taking turns rolling dice in a combat challenge.
This is just a personal preference of mine. Let the DM decide when the dice are required to come into play as opposed to the players trying to force the issue. The best way to do this is for the player to make a request to attempt a goal (like you did indicating that you wanted to find and question a slave) and let the DM decide the mechanics for that (a skill roll(s) is required and if so, which one(s); or the PC is automatically successful; or a skill challenge is needed, etc.). If a skill roll is required, the DM can speed that up in PBP by just rolling for the player when he posts his response.
Trying to cut to the chase by jumping into the DM's sandbox can become counterproductive as per the examples above. IMO. I'd rather that the DM decide the flow of the game as opposed to a non-asked for dice roll. JMO.
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