There are essentially 4 different levels of competency that characters can have with a given Skillset/Basic Ability:
- untrained: an unmodified d20 roll
- expertise: a d20 roll where a 1 is treated as a 20
- trained: a d20 roll, modified by adding a d6 roll
- trained+expertise: a combination of both; a 1 on the d20 is treated as a 20, and a 1 on the d6 is treated as a 6, and both rolls are added together
A success is when the result is in the 10-19 range, with anything lower being a failure, and anything higher being a critical success, as outlined in the rules. However, on top of this, the "DM" needs to make additional considerations when asking for a roll -- which also brings up the key consideration that players should not just roll skills, unless prompted by the DM.
Essentially, the players should be describing a desired action or course of action to the DM; from there, the DM judges whether this aligns with a skill (or skills) and asks for a roll if one is necessary. How is that determination made? Well, generally there should be an understanding within the group of what level of "magic" or "fantasy" (or "realism") their campaign entails; depending on this, some actions may be trivially easy, challenging, or impossible.
If something is either "trivially easy" or "impossible," then the DM should not ask for a roll, and should explain as such; a trivially easy task just succeeds, and an impossible one cannot even be attempted, or the characters know it cannot succeed, forcing them into an alternate course of action. Whether something is trivially easy (or challenging) can be weighed against a particular character's competency with an applicable skill. For instance, a character with both training and expertise in climbing may be able to treat that action as not requiring a roll (under certain circumstances) while an untrained character in the same circumstances must make a roll (as it is effectively "challenging" for them.)
The other consideration to make when asking for a roll, is whether failure is realistic or interesting, and what the outcome of the failure could (or should) be. If there is nothing "at stake" then there's no sense in rolling.
The specific example that often comes to mind is "picking a locked door." If the characters are being chased, there is a time pressure; failure to pick the lock means the protagonists have lost time, during which their pursuers have gained ground on them. If the characters are trying to be subtle, then a failure to pick the lock means that the door must be broken down -- this solves the problem in a way that can increase the odds of detection, either by being loud, or the prospect of leaving behind evidence of their presence (in the form of the destroyed door.)
So where does this leave having Advantage on a roll?
Well, the intention of this mechanic (as it pertains to skill checks) is to provide characters an opportunity to spend a limited resource, and gain a better chance of success on a skill that their character would normally not perform well at. Narratively, this can be described as a feat of superhuman perseverance, sheer willpower, adrenaline, magic, or just plain luck -- as the player sees fit. Mechanically, using Advantage on a skill roll should not cause an adjustment of the difficulty, once it has been established that a roll is needed for success. Advantage (statistically) has a comparable success rate to making a trained skill check -- the difference is in the chance for critical success, which is much more likely on a trained check.
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As an aside, the classes from the slate "Heroes of the Wilderness" (that use a class die other than d6) were all given additional skill mechanics, utilizing their class die -- either instead of, or in conjunction with their "training" die. Since this slate of classes is more narrowly focused in terms of theme (and therefore skills) I felt it was fair to give them a little extra boost to their skills. I had already worked out most of the math for these mechanics, so I wanted to use them somewhere, and this seemed like a reasonable fit. If there is negative feedback about the resulting mechanics, I will probably just take them out.
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Schedules are a little disjointed as of late, but I'm still hoping to get 3 posts in this month; next post will be in 7 or 8 days, most likely.
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