So the way I understand it, if you have the appropriate proficiency you can help with almost any skill check provided that there’s something you can actually do to help.
The imp is proficient in Deception, Insight, Persuasion, and Stealth.
The sprite is proficient in Perception and Stealth, the quasit and pseudodragon with Stealth.
So... the sprite could help you in making perception checks ranging ahead of the party together looking for traps, or the imp assist you with the knowledge it has of mortal bargains using deception or persuasion checks, or insight checks as it tells you what it knows of the mortal desires that drive the people around you. So your familiar can basically give you advantage in most social situations, and assist you in rogue like scouting and stealth.
Advantage on three different skill checks is no laughing matter.
So the way I understand it, if you have the appropriate proficiency you can help with almost any skill check provided that there’s something you can actually do to help.
The imp is proficient in Deception, Insight, Persuasion, and Stealth.
The sprite is proficient in Perception and Stealth, the quasit and pseudodragon with Stealth.
So... the sprite could help you in making perception checks ranging ahead of the party together looking for traps, or the imp assist you with the knowledge it has of mortal bargains using deception or persuasion checks, or insight checks as it tells you what it knows of the mortal desires that drive the people around you. So your familiar can basically give you advantage in most social situations, and assist you in rogue like scouting and stealth.
Advantage on three different skill checks is no laughing matter.
Paladin - warforged - orange