Optimizing 4 charismatic characters.

[Georlik]

Me and my friends are starting an Out of the Abyss adventure on Wednesday. We decided to play as half-siblings and, coincidentally, we all chose dexterous charismatic half-elves and humans:
Paladin (Oath of the Ancients)
Sorcerer (undecided origin)
Bard (undecided school)
Warlock (some kind of multiclass with Necromancer for fluff purposes)

Any advice on how to synergies them properly?

[Citan]

Me and my friends are starting an Out of the Abyss adventure on Wednesday. We decided to play as half-siblings and, coincidentally, we all chose dexterous charismatic half-elves and humans:
Paladin (Oath of the Ancients)
Sorcerer (undecided origin)
Bard (undecided school)
Warlock (some kind of multiclass with Necromancer for fluff purposes)

Any advice on how to synergies them properly?
Hi! ;)

Well, basically anything could go because there roles are very complementary.

So what I'm gonna say are only suggestions, wild ideas but not specifically the "best way" or anything like that.

Considering that...
Martial-wise
- Paladin is near always in melee
- Warlock and Bard can be geared towards melee (barring Sorcerer because I suppose you are restricted to official material, otherwise Favored Soul Sorcerer could be the best choice).
- and having only one melee guy could be not enough...

Offensive spells-wise
- Sorcerer will easily cover AOE spells and get also some control.
- Warlock can take some AOE spells as well as some debuffs.
- Bard has nice debuffs, but you could benefit greatly from early Magic Secrets.

Healing/buffs-wise
Bard gets Healing Word, Paladin gets Bless/Shield of Faith, later Sorcerer can grab Haste so the basics are here.
Early Magic Secrets could be nice though to round up.

Utility-wise
- You have as is no ritual casting, so while Bard and Paladin can cover a bit on the utility side it eats at their spell learnt/prepared. One could take the Ritual Caster feat, but it requires a INT/WIS requirement and the list is somewhat restricted. Warlock gives a nice solution though with Tome Pact.

I'd suggest the following.

Paladin Ancients
Leveling: start with STR and CHA, grab Sentinel so he can limit at most enemy movement and/or GWM to make heavy hits. Usually cast Bless on himself and two others (the other melee guy and Sorcerer). Another good feat later could be Mobile (because you will usually be the primary target/the most exposed, getting free Disengage and extra mobility could be nice to avoid getting surrounded and such). Wield a shield if you feel you are taking too many hits, start with a good Constitution if possible.

Role:You are the one preventing enemies to hurt your friends. First by killing them as fast as possible. Second by, when not possible, using a Command to apply some soft control. You will usually spend your slots and concentration on Bless, but when you feel it's useful, like against a big one, don't hesitate to instead use a smite spell or Compelled Duel. These can change the power level of the encounter. Also don't forget you have MoonBeam prepared. At higher level, it can help greatly in channeling enemies in the way you want.


Warlock
Leveling: start witht DEX and CHA, grab Hex and Armor of Agathys at first, along with Eldricht Blast and Booming Blade. Be a Fiend Warlock to get THP on kill. As you level, grab Repelling Blast and "Mage Armor" first . At level 3, grab Tome Pact with Shillelagh, Guidance and whatever you wish as the third. Then take the "free Rituals" Invocation asap. Later, you can grab Agonizing Blast (and even Eldricht Spear) and GreenFlame Blade.

Role: your role will vary as you can adapt: you can engage fight with Hex & Eldricht Blast and usually deal damage from afar. When the Paladin needs help to stand the frontline, you can engage with the support of your THP and Armor of Agathys, using Shillelagh-enhanced quarterstaff with Booming Blade or GreenFlame Blade to deal decent to good damage.
Out of encounters, you can take care of all support/utility, such as putting a Tiny Hut or Alarms, Identify things etc (as long as your DM provides you regular chances to learn such rituals).


Sorcerer
Leveling: be the blaster, by taking Draconic Sorcerer (fire recommended, but any can work): start with DEX and CHA to take advantage of permanent Mage Armor, grab Ray of Frost, GreenFlame Blade and Shocking Grasp. Pick up the usual basic spells (Shield/Magic Missile) and AOE spells (Burning Hands), swapping as necessary when you stop using some. Your spells of choice will be Scorching ray and Fireball obviously, don't forget to also take some control/buffs spells such as Haste or Slow. When you learn other cantrips, Chill Touch can actually be a nice... Touch. :)
Good choice of Metamagic:
- Subtle: not very useful in fight, but great in any other occasions.
- Twin: probably the one you should pick whatever happens, because works with many buffs and offensive spells alike.
- Quicken: another good choice, if you want to keep your action for anything (like a cantrip for extra damage, or Dash/Dodge). But not mandatory for you.
- Careful spell: allows you to spare your allies for any spell you cast. Could be a great choice depending on how your team actually plays (like, being able to drop a Fireball or Stinking Cloud on a group that surrounds your Paladin friend, without harming him).
- Heightened: one of the few ways you can lessen the chances of saves against a spell, and some spells you learn can be game-changers.
All are good choices, I'd have a slight preference for Twin and either Careful or Heightened though for your particular group, but really choose whatever you prefer.

Role: as the Warlock, you will usually hang in the back, but thanks to weapon cantrip and decent natural armor (along with Mirror Image when needed) you can fend for yourself in melee when necessary.
Your role will be to choose whether to buff/debuff depending on the situation, and take care of the swarms of weaker enemies. On a mundane turn, you can apply damage and soft control with cantrips.


Bard
Leveling: start with CON and CHA, grab Healing Words, Vicious Mockery and Dissonant Whispers. You can go Human Variant if you'd like to grab Magic Initiate or Spell Sniper, allowing you to get more offensive cantrips (including SCAG ones if you have a good DEX, otherwise i'd suggest Eldricht Blast and/or Shocking Grasp). Inspiring Leader will be another feat of choice later.
Go Lore Bard: your Cutting Words will help your group defensively, and you can grab Magic Secrets as early as level 6, allowing you to pick 2 spells among the following: Slow, Haste, Aura of Vitality, Conjure Animals, Spirit Guardians, Counterspell, Bless.
My suggestions would be Conjure Animals (because you can use it for scouting, as a live wall, or extra offense, it's one of the most versatile), the second depending on your experience up to this point...
- you are often using too much resources on healing? Aura of Vitality.
- you encountered a bunch of casters? Counterspell ASAP.
- you often find yourself in trouble and/or it's difficult for your group to keep clear front lines & back lines defined? Spirit Guardians.
- your Sorcerer pal usually spends his Concentration on a Haste so he can't debuff? Grab Slow.
- your Pal friend never uses/sustains Bless for whatever reason? Then grab it.

Your role will be to debuff with cantrips and spells, while keeping everyone up with Healing Words. When you have nothing special to do, an offensive cantrip will do the trick.

Hope this detailed suggestions will help you. Note that I didn't include any multiclassing because 1) does not seem necessary (although it could help) 2) makes things much more complex to describe. XD
For a very quick preview of what you could do:
Bard: take 1 dip in Life Cleric to be extra good at healing (then pick Aura of Vitality).
everyone: dip Rogue 2 for Cunning Action and Expertise, helping you cover skills that don't rely on CHA/DEX. ;)

[Georlik]

Hi, Citan! And greetings to everyone (where were my manners?).
This is an awesomesauce. Such extensive reply almost dubs as a guide.
I'll be playing the Paladin, so no worries of party not having bless. Also I'm thinking of being a Dex paladin: no GWM for me, but no stealth penalty for the group either! Mobile is out of question though - if I am running away from the enemies, they focus my squishier friends. And that simply will not do. Nice observation of having no rituals though, I'll check with our Warlock of his pact of choice. Any advice on optimizing them for ranged combat? I think that would be a safer choice (?) given the lethality of early levels.

[Gastronomie]

Sorcerer, Warlock and Bard are all good at ranged attacks (Warlock in terms of damage, Bard in terms of control effectiveness). Fire Bolt or Ray of Frost for Sorcerers, Eldritch Blast + Agonizing Blast invocation for Warlock (add Repelling to also move away the enemies and make sure the backrow guys can flee out of melee range), Vicious Mockery for Bard. You have enough ranged attacks.

If you're worried about dying, have the Bard also pick up Cure Wounds or Healing Word. Two healers is usually enough.

[Citan]

Hi, Citan! And greetings to everyone (where were my manners?).
This is an awesomesauce. Such extensive reply almost dubs as a guide.
I'll be playing the Paladin, so no worries of party not having bless. Also I'm thinking of being a Dex paladin: no GWM for me, but no stealth penalty for the group either! Mobile is out of question though - if I am running away from the enemies, they focus my squishier friends. And that simply will not do. Nice observation of having no rituals though, I'll check with our Warlock of his pact of choice. Any advice on optimizing them for ranged combat? I think that would be a safer choice (?) given the lethality of early levels.
Well, I didn't dare suggest a DEX Paladin because of various reasons, but that is a very good choice also. ;)
About Mobile, don't forget that you can use it for other reasons than running away. Extra 10 feet means that in some occasions you will reach in time enemies that would have "waited" another turn otherwise. "Free Disengage" means that you could go "out of your way" to attack an enemy that tries to avoid you by going around and go back on your "guard" position, or sacrifice one attack to run past one big enemy to reach and kill a squishy caster that was protected behind...

I agree though that it's not the best feat for you. Warcaster or Shield Master would be of better interest because you can further enhance your resilience by wielding a shield.

And being DEX-based means you can also just use a longbow when you cannot hit in melee for whatever reason. For others, as Gastronomie said, no problem: Warlock gets Eldricht Blast, Sorcerer gets Ray of Frost (or Firebolt), Bard gets only Vicious Mockery by default but it can help Paladin. Or, as I said, suggest him to grab either Magic Initiate: Sorcerer (Ray of Frost/Firebolt/Chill Touch for ranged, Shocking Grasp/GFB/Booming Blade for melee, and you can get Mage Armor also) or Spellsniper: Warlock (Eldricht Blast). Or directly dip Draconic Sorcerer / Warlock if other features interest him. I would recommend the Magic Initiate option though, because if Spellsniper, he would feel underpowered compared to the Warlock, and if dipping he would be directly overstepping onto Warlock's identity.

Since you are all DEX+CHA-based, you could all profit very much from Rogue dip: the whole party would be expert at stealthing with great infight mobility from Cunning Action, maybe even going Swash 3 for extra initiative. Too bad you start at level 1, making this a bad idea.
If you had all started as level 5-6 characters though, I would have strongly suggested this: perfect balance mechanically so you could be a deadly team of silent strikers, and could easily explain how/why you know each others, like ancient friends from a Rogue brotherhood who went their own way, before gathering again for a particular mission years after... xd

Note though that, now that I know you all want to focus on stealth, an option of choice for Lore Bard's Magic Secrets would be Pass Without Trace. ;)

[Ashrym]

Utility-wise
- You have as is no ritual casting, so while Bard and Paladin can cover a bit on the utility side it eats at their spell learnt/prepared. One could take the Ritual Caster feat, but it requires a INT/WIS requirement and the list is somewhat restricted. Warlock gives a nice solution though with Tome Pact.

Bards are ritual casters. The only caveat is they don't pull rituals from a book like wizards and spells known (the requirement for bard rituals) is less than what clerics or druids can pull off so the only caveat there is they don't tend to have a lot of rituals learned. Given it would probably be worth taking a couple regardless as a consideration because filling out a ritual book isn't much of a guaranteed process.

My latest bard was an outlander (pilgrim) listening for nature's song and using music to soothe savage beasts. Very thematic instead of optimized and intentionally focusing on rituals in the theme to make up some quantity over quality in the spells. He plays like a combination of a Disney princess and Dr. Doolittle, and does do veterinary work and animal husbandry. His current list of rituals include detect magic, identify, speak with animals, locate plants or animals, animal messenger, and beast sense. Other spells are animal friendship, heroism, speak with plants, plant growth, conjure animals, and polymorph. Skills are athletics, survival, nature, history, animal handling, medicine, persuasion, perception, and insight. Expertise was in animal handling and nature. The variant human feat was healer.

Obviously not optimized but it doesn't take much to swap out 2 or 3 spells and maintain the theme for a stronger list. The character knows what animals would be in the area based on skills and what to look for with locate animals for scouting and information, mounts, and possible combat help. The only spells on which I'm spending first and second level slots are animal friendship and heroism. His specialty is tracking down exotic beasts and training them. The point is that a lore bard can fit in a few useful rituals.

[Citan]

Bards are ritual casters. The only caveat is they don't pull rituals from a book like wizards and spells known (the requirement for bard rituals) is less than what clerics or druids can pull off so the only caveat there is they don't tend to have a lot of rituals learned. Given it would probably be worth taking a couple regardless as a consideration because filling out a ritual book isn't much of a guaranteed process.
...
The point is that a lore bard can fit in a few useful rituals.
You're right, my miss, I should have been more precise.
But I think my point still stands.

As you stressed, a Bard must eat at his known spells to get a few ritual spells, and he must choose carefully. It means either knowing in advance that a particular ritual (such as Speak with Animals) would be particularly useful, and also deprive oneself from other great non-ritual spells, some of which are rarely available. And there are some great ritual spells Bard just doesn't have access to.

If nobody else was available, sure, it would be worth for a Bard to learn a few rituals (such as Animal Messenger, Silence and obviously Leomund's Tiny Hut).

Considering OP has a Warlock in his party, seems much better to me that the Bard just let him take all of these (and potentially all rituals) with the invocation so himself can focus on all great spells only he has access to.

[Georlik]

Thank you all for the input. After much consideration the party consists of:
Half-Elf Paladin (straightforward Acolyte of Lathander)
Human Undying Warlock (pupil of a Red Wizard with a Sage background)
Half-Elf Bard (she is a Folk Hero with faerie motifs)
Wood Elf Rogue (a Spy with outlander feature who strives to become a bladesinger)


Our party's theme is "unlikely siblings" similar to Konoha Team 7 in terms of intercommunication (with Naruto, Sasuke, Sakura and Kakashi respectively). They all are offsprings of either an elven mother or human father (both in half-elven case) hailing from Aglarond.

The game starts in a few hours. We'll see how it goes.

[Ashrym]

You're right, my miss, I should have been more precise.
But I think my point still stands.

As you stressed, a Bard must eat at his known spells to get a few ritual spells, and he must choose carefully. It means either knowing in advance that a particular ritual (such as Speak with Animals) would be particularly useful, and also deprive oneself from other great non-ritual spells, some of which are rarely available. And there are some great ritual spells Bard just doesn't have access to.

If nobody else was available, sure, it would be worth for a Bard to learn a few rituals (such as Animal Messenger, Silence and obviously Leomund's Tiny Hut).

Considering OP has a Warlock in his party, seems much better to me that the Bard just let him take all of these (and potentially all rituals) with the invocation so himself can focus on all great spells only he has access to.

I went heavy on rituals because the party consists of my lore bard, chain pact feylock, ancients oath paladin, totem barbarian, and champion fighter. The campaign is set in a lost island jungle which is why the nature motif influencing the group. I'm the nature specialist. Locate animals, speak with animals, and animal friendship are very useful for the setting while rituals stretch out bard slots a lot in the given environment.

I agree that it seems like I've eaten spells known and it's basically true but the alternative is that I can cast the spells normally because I know them and that gives me the option to use those spells without breaking concentration. That's not different from druids or clerics needing to give up prep slots and have the same advantage of using the spells normally or as rituals, although both of those classes can choose not to prep rituals unless they expect to use them and clerics or land circle druids have a lot of prep slots early. Wizards, tome warlock, and ritual caster feat users don't have that option. They cannot cast an action ritual as an action when a person might want to cast it faster and they will have to give up concentration to cast such rituals. It's a less common case but sometimes I want to cast those spells without waiting or breaking concentration on polymorph. There are two sides to that coin.

Tome warlock is a good suggestion for rituals but I found I had to break concentration on spells to use rituals or avoid concentration more than I might on a class that didn't use rituals. I also found that only having a choice of one first level ritual spell and random luck or DM generosity didn't necessarily give me a lot of choice in the rituals to which I had access, which is the same issue that can occur with the feat.

That's why I think it's good to choose good rituals on the bard anyway. They can be swapped out leveling if the tome warlock finds them to add to his or her ritual book. Knowing the type of campaign and setting can influence what might be considered good or not.