Li Shenron
Legend
Our Rogue has just reached 3rd level, and is very undecided on which archetype to choose... want to help? 
Some details about the Rogue character:
- takes care of most group's exploration tasks, but is perhaps more interested in combat (mixed melee/ranged)
- human with fairly high Dex/Con/Int, rest is average
- has the Charlatan background (knows Disguise and Forgery kits, but hasn't actually used them ever)
- expertise in Stealth and Investigation, proficiency in Acrobatics, Sleight of Hand, Perception and Deception
And about the rest of the party and the campaign:
- Cleric of Life, focused on healing and melee combat
- Moon Druid, focused on combat wildshape and out-of-combat spellcasting
- Fighter (archetype to be decided), focused on melee combat
- currently playing the old Horror on the Hill module, minimal social interaction otherwise plenty of exploration and lots of combats
- most of the times we run combats in TotM mode; unfortunately this means that the Rogue hasn't learned to take advantage of the Cunning Action ability
- the whole campaign is a family game with kids 7-11yo
Story-wise the player is very open, so all archetypes are fine. We only have the core books however, so it has to become either Thief, Assassin or Arcane Trickster.
Since our players are at their first 5e campaign, I first suggested the Thief archetype, being it the most "normal" from a narrative point of view. However, it looks very underwhelming to the point that I am not sure its abilities will ever come up! Fast Hands is for combat use, but how often do you actually expect to pickpocket someone or disarm a trap or pick a lock during combat? Second-Story Work bonus to climb speed also is only relevant in combat, but uncommon (especially in TotM, we don't keep track of precise distances). They sound like they require an extremely creative player to put into good use. Even Supreme Sneak while certainly it will be used all the time, it still doesn't feel special. Beyond those, other benefits are too far away in the future (Thief's Reflexes looks awesome, but we'll never get there).
The Assassin archetype may have some moral issues, but perhaps I can narrate the concept in a way that removes the evil shades. The bonus proficiencies are worthless for this character, but the Assassinate bonuses in the first round are definitely going to be very useful. Then it's probably the end of it, considering that Infiltration Expertise is similar to the Charlatan's feature that has also been unused so far.
The Arcane Trickster can actually be the best addition to the group, considering that we have no Wizard-types. Even if it's just a few spells, they will certainly become handy both in and out of combat. The downside is that the complexity of the character is increased significantly.
So in a summary:
- Thief: (+) most classic character, (+) encourage creativity but (-) if you don't keep up with that, the abilities are useless
- Assassin: (+) easy and powerful boost in combat at level 3, then (-) basically that's it, and (-) requires some narrative care to eliminate the evil bent
- Arcane Trickster: (+) best all-around addition to the party, (-) more difficult to play and resource-manage
What would you suggest?

Some details about the Rogue character:
- takes care of most group's exploration tasks, but is perhaps more interested in combat (mixed melee/ranged)
- human with fairly high Dex/Con/Int, rest is average
- has the Charlatan background (knows Disguise and Forgery kits, but hasn't actually used them ever)
- expertise in Stealth and Investigation, proficiency in Acrobatics, Sleight of Hand, Perception and Deception
And about the rest of the party and the campaign:
- Cleric of Life, focused on healing and melee combat
- Moon Druid, focused on combat wildshape and out-of-combat spellcasting
- Fighter (archetype to be decided), focused on melee combat
- currently playing the old Horror on the Hill module, minimal social interaction otherwise plenty of exploration and lots of combats
- most of the times we run combats in TotM mode; unfortunately this means that the Rogue hasn't learned to take advantage of the Cunning Action ability
- the whole campaign is a family game with kids 7-11yo
Story-wise the player is very open, so all archetypes are fine. We only have the core books however, so it has to become either Thief, Assassin or Arcane Trickster.
Since our players are at their first 5e campaign, I first suggested the Thief archetype, being it the most "normal" from a narrative point of view. However, it looks very underwhelming to the point that I am not sure its abilities will ever come up! Fast Hands is for combat use, but how often do you actually expect to pickpocket someone or disarm a trap or pick a lock during combat? Second-Story Work bonus to climb speed also is only relevant in combat, but uncommon (especially in TotM, we don't keep track of precise distances). They sound like they require an extremely creative player to put into good use. Even Supreme Sneak while certainly it will be used all the time, it still doesn't feel special. Beyond those, other benefits are too far away in the future (Thief's Reflexes looks awesome, but we'll never get there).
The Assassin archetype may have some moral issues, but perhaps I can narrate the concept in a way that removes the evil shades. The bonus proficiencies are worthless for this character, but the Assassinate bonuses in the first round are definitely going to be very useful. Then it's probably the end of it, considering that Infiltration Expertise is similar to the Charlatan's feature that has also been unused so far.
The Arcane Trickster can actually be the best addition to the group, considering that we have no Wizard-types. Even if it's just a few spells, they will certainly become handy both in and out of combat. The downside is that the complexity of the character is increased significantly.
So in a summary:
- Thief: (+) most classic character, (+) encourage creativity but (-) if you don't keep up with that, the abilities are useless
- Assassin: (+) easy and powerful boost in combat at level 3, then (-) basically that's it, and (-) requires some narrative care to eliminate the evil bent
- Arcane Trickster: (+) best all-around addition to the party, (-) more difficult to play and resource-manage
What would you suggest?
