Making the Most of a Duelist Healer (Cleric/Rogue)

[Enyo]

Hey, guys.

While thinking of characters to fill up my roster for future campaigns, while assuming the level 20 cap, I thought of making a charmer who specializes in healing as well as being one-on-one with enemies and maybe sneak attack. Obviously not someone who'd stick around in the front lines for sustained fights.

Problem is, I can't really find any builds for feats and equipment aside from a rapier, so I'm having a difficult time to not make that concept fall flat on its face when it comes to combat. Here's a bit of the specs:

Race: Human male

Cleric Domain: Life

STR:11
DEX: 15
CON: 10
INT: 13
WIS: 16
CHA: 14

Background: Noble

Skills: Acrobatics, Athletics, Medicine, Persuasion, Perception, and Stealth

Feats?: Defensive Duelist

[Citan]

Hey, guys.

While thinking of characters to fill up my roster for future campaigns, while assuming the level 20 cap, I thought of making a charmer who specializes in healing as well as being one-on-one with enemies and maybe sneak attack. Obviously not someone who'd stick around in the front lines for sustained fights.


Hi!
I think your concept of one-on-one healing striker would be a bit easier to do with CHA-based classes ("Compelled Duel" from Paladin *especially fun with Vicious Mockery*, "Charm" from Bard/Sorcerer, "Healing Word" available to Bards, "Swashbuckler" Rogue archetype with CHA-based bonus), where Life Cleric would be a dip.
But hey, concept first, so if you're set on being a Cleric as main... :)
WIS-based or DEX-based abilities that could fit in...
Note: these are all independant propositions, not "take everything". :)

Druid ? : At least 1 level for cantrips (Thorn Whip) and "Charm Person / Entangle" spells. Maybe 2 levels as Land to gain Arcane Recovery (and more levels if you like the spells, but you'll lose high-level spells).
Rogue Thief archetype: Assassin is totally opposite to your concept, Swash is reliant on CHA, Trickster on INT. Thief gives you climb, USE OBJECT AS BONUS (welcome healing kit) and Magic Device.
Ranger Hunter archetype, 5 : At least 5 for Fighting Style (Dueling), Extra Attack, Colossus Slayer (synergizes well with SA) and 2nd level spells.
Fighter : action surge at level 2, extra attack lvl5, BattleMaster archetype is nice to keep enemy.

With that said, it all depends on what you want to focus on. Multiclass in non-spellcaster makes you lose high-level spells fast. So first decide on that: "which high-level spells do I want for this build" and "is my focus Healing or Damage"?

1. High Spellcasting AND Healing >> either Fighter 2 for action surge, or Thief 3 for Bonus "use object" (extra nice with Healer feat).

2. High Spellcasting AND Damage >> Druid 2 can be nice, you'll be dealing damage with spells only though (Alternative : Druid 1 for Shillelagh, Paladin 2 for Divine Smite but requires STR and CHA 1 so it's very Multi-Ability Dependent).

3. Moderate Spellcasting and Healing >> keep 5 to 8 levels to use on other classes (ex Ranger 5, Druid 1). 5 levels max keeps 8th level spell.

4. Moderate Spellcasting and Damage >> As a main Cleric you'll have... Either to keep 7th lvl spell, then it's a similar choice to above. Either to really focus on physical damage, then Rogue bests Ranger from 7th level and beyond. But you severely hampers spellcasting.

5. Limited spellcasting, Damage (does not seem your objective though): Cleric 8 / Rogue 12 (best for ASI/Feats) OR Cleric 9 / Rogue 11 (at least one 5th level spell) or Cleric 7 / Rogue 13 (not recommended even if Use Magic Device is good).

As for feats: if you go ranged SharpShooter is nice, otherwise...
Warcaster always good for a healing melee especially for CON save on concentration.
Shield Master also if you plan on using a shield.
Healer with Thief, unless it is ruled that you HAVE to use an action as per Healer description, I'm note sure.
Alert: always good to be first.
Resilient/Durable/Mobile/Elemental Adept/Crossbow Expert: good or no depending on your style and number of ASI...

My 2 cents. :)