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At first, you might hit F5, march right up to the enemy and try for a dialogue check, but if that fails...
Split everybody up, place them into position, go for a long-ranged surprise attack to begin combat, and then wipe the enemy out, using the Rogue wisely.
If things go to hell again, reload. Try something different.
Eventually, you'll be much better on the approach.
If my character were a Rogue, I would still try for the dialogue checks first before I went into military mode.
Just hit F5 if you see danger ahead.
Thanks for your input though, glad I'm not just overseeing something. Just sub-optimal design.
Choose one.
On a more helpful note, as a rogue, come level 2 you can hide as a bonus action, so if you maneuver yourself correctly in the battlefield, you'll be able to reenter stealth and do sneak attacks. Just keep out of the red detection zones and you'll be alright. Remember that you can also sneak attack with ranged attacks.
Flanking is also a rogue staple for sneak attacks, as is attacking CC'd targets.
Playing a rogue like a fighter is a recipe for disaster. You need to go out of your way to set up a sneak attack before you attack, as that's the source of your damage. Then get away (like with disengage) so you're not eating every melee attack
Yes you are:
1. Your rogue MC should have DEX as main stat and not much in the way of CHA. CHA is used for talking so your MC should not be the party "face". If you don't play a high CHA character yourself the companion available to do the job is the warlock Wyll. He has the required CHA.
2. Mechanically what you do is move your MC back out of the way somewhere, preferably in shadows, and send forth your party "face" to speak to the NPCs. If it's Wyll you probably want to send your fighter/barb and your cleric along with him to protect him, he's not the squishiest caster but he's still a bit squishy. That way if things go south and all hell breaks loose your MC will be able to do all the sneaky stabby stuff no problem.
3. Your party needs to fulfil five roles:
1. Melee combat specialist
2. Support healer/buffer (can be bard, druid or cleric)
3. Utility - locks, traps etc and stealing if that's your bag
4. Offensive magic user
5. Speech specialist - the "face"
Since you only have four characters in your party one has to fulfil two roles. Your rogue MC fulfils the utility role (as well as doing sneaky stabby stuff). Therefore you need a high CHA character to be the "face" and also fulfil another role.
The classes that can do this (i.e. the classes that also use CHA as their main combat stat) are paladin, warlock, sorcerer and bard. All four can be the "face", The paladin also covers the melee combat role, the warlock and sorcerer also cover the offensive magic role and the bard can also cover both the support healer/buffer and the utility roll (the bard can cover a lot).
Thus since you are playing a rogue Wyll is only available companion you can use as a "face".
If after reviewing this you either a) want to play the "face" yourself as many players do or b) don't like Wyll and don't want to play with him your best bet is to restart with a suitable high CHA "face" class MC.
Paladin, warlock and sorcerer are all very good, in fact they all kick serious arse in combat, but the bard is a bit more advanced since although they can do a lot they are a bit of a jack of all trades and master of none which is great if you know what you are doing but can be tougher if you are a beginner.
Or if you want to go full pro you could also consider a Sorlock which is two or three levels of Warlock (for the killer Eldritch Blast cantrip) and 9 or 10 levels of sorcerer. This is an extremely strong multi-class build that that kicks all sorts or arse as well as making an excellent "face". You would have no trouble finding a good build guide for it, it's very popular in 5e circles.
Brilliant and thought out post. This is very helpful. Thank you.
Also your "sneak attacks" automatically proc when you hit an enemy within 1.5m of an ally, so just focus whoever is standing next to your ally with melee or ranged. If you land a hit, a d6 will roll to add the damage. That d6 btw scales with your level, it gets pretty absurd the higher level of a rogue you get.
I would also suggest going Arcane Trickster, you can learn some good spells and cantrips to help be more sneaky like Invisibility.