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Rhenny said:Or, should a DM just let PCs that seem to have key requisites succeed without rolling at all? (i.e Cleric with training in Religion should be able to automatically succeed on a DC 10 Religion check)
Mostly, this.
Back during the playtest for 5e, they floated a skill/ability check system which involved mechanics for automatic successes. They were decent, but really not very different from the DM just winging it and saying "You know, what, yeah no need for a check, your character has the acolyte background and proficiency with Religion, so she would be able to lead this religious ceremony in her sleep."
There is one additional trick I've used.
In order to get the automatic success, make some sort of story requirement that the character needs to fulfill through...adventuring! They need to explore, interact with NPCs, or fight monsters to meet those requirements. So, for the ceremony, maybe the PC needs to have a certain level of Renown in the settlement, to retrieve a chalice stolen by goblins, etc.