5-Rogue Shenanigans.

[FaceofBo]

I've been doing some theory-crafting, and I realized, it'd be completely viable to have a full party of Rogues, and have a decent spread of skills-uses. I mean, with the Grappler feat, you could easily make a strength based Enforcer kinda guy, then you've got the rest of them as the basic Assassin, Trickster, Thief, and Swashbuckler. I mean, no it wouldn't be the most optimized party, but it could definitely has some weight behind it. Thoughts?

[Mortis_Elrod]

I've been doing some theory-crafting, and I realized, it'd be completely viable to have a full party of Rogues, and have a decent spread of skills-uses. I mean, with the Grappler feat, you could easily make a strength based Enforcer kinda guy, then you've got the rest of them as the basic Assassin, Trickster, Thief, and Swashbuckler. I mean, no it wouldn't be the most optimized party, but it could definitely has some weight behind it. Thoughts?

Drop the Assassin and add Mastermind, Enforcer can be a Inquisitor rogue. Now you almost have a full heist team. Mastermind who is the team leader, Trickster for spells, Thief for good scouting and thievery (could be switched with the Scout option), Swashbuckler face, And the Muscle/Lie-detector/Interrogating guy of Inquisitor .

Alternatively everyone go for max dmg builds and be ninjas, sent out to kill one target at a time by your shogun.

[Specter]

Yep. Even with two Rogues (Mastermind and Arcane Trickster) you could run a full-on buddy cop adventure.

[Cap'm Bubbles]

I've been in a group with 4 rogues (assassin, arcane trickster, thief, and mastermind). We had a champion as well for an enforcer-type.
Any type of stealing went off without a hitch, magical protections or not.

Combat was...swingy.

Whenever we could pull off an ambush, half the time there wasn't a round 2. Our Mastermind happened to be the most experienced among us and thought of some great ways to get more use out of basic items as more weapons, which got us some more mileage out of this squad.

Offense, though great, could not handle more than a handful of enemies at a time. It was a burden on our one fighter to be the tank, not only with HP, but also with AC. Some would try to get in melee range with him, but simply didn't have the staying power to make a difference long enough to ease the pressure. At some point, your enemies (or DM) will stop bothering with the tank and have every enemy that can make ranged attacks target a single rogue.

To illustrate, we ended up in a fight against an assortment of 100+ minions (satyrs and other greek-themed enemies), with only positioning/timing and a sorcerer ally as our advantages. Not 100 in a dungeon parcelled out by room, but 100+ active and with initiative. All of us were at level 8.
AoE attacks ran out of slots, forcing the remaining 30~enemies to deal with the party in melee and short range. Rogues did a great job taking down every enemy that ended its turn within range of our tank, but took too much damage from the shear number of ranged attacks still coming in. Though ultimately victorious, 2 party members were dead, and a 3rd survived only through a last chance misty-step->health potion by the arcane trickster.

It's a great experience as long as everyone wants to play a rogue and the DM doesn't put you in combat-is-war situations. Evasion and uncanny dodge result in more than double effective Hitpoints, and cunning action helps make up for the limited AC available to rogues. No single target will last long enough to matter. BUT, crowd control can only be achieved by tactics and positioning rather than by class abilities. You are encouraged to play as a smart group, both through role-play and in combat. And because of that, having proficiency (or even double) in every skill in the party opens up more opportunities than even a larger mixed party would otherwise have.

[JellyPooga]

To illustrate, we ended up in a fight against an assortment of 100+ minions

Uh...I'm not entirely sure any group of 4-5 level 8 characters would reliably be able to handle a combat of that scale without a hitch (unless specifically built/prepared for dealing with large scale combat). It hardly speaks against Rogues that you struggled with crowd control under those circumstances. There's also the question of what kind of Rogues you were playing; Rogues are remarkably capable of weathering a lot of damage if built right and if you're playing a game where you know combat endurance is going to be a key survival skill, then it probably speaks more to your groups lack of foresight in that regard than anything about the Rogue class itself.

[FaceofBo]

Drop the Assassin and add Mastermind, Enforcer can be a Inquisitor rogue.

Probably should have clarified, the Enforcer guy is a Mastermind. He's a Hill Dwarf with the Grappler Feat, so he grapples his target, gets advantage, and then just shanks his target to death while pinning them to the floor.

[djreynolds]

Probably should have clarified, the Enforcer guy is a Mastermind. He's a Hill Dwarf with the Grappler Feat, so he grapples his target, gets advantage, and then just shanks his target to death while pinning them to the floor.

I always wanted to run A Reservoir Dogs style campaign

[FaceofBo]

I always wanted to run A Reservoir Dogs style campaign

I honestly thought it just sounded like so much fun to play a city-scape campaign and just have this little gang that grew bigger and scarier, and I also wanted to see if I could make an all-Rogue party. These guys were the results, I actually went and fleshed them all out, spec-ing them out and it actually works really well.

[djreynolds]

I honestly thought it just sounded like so much fun to play a city-scape campaign and just have this little gang that grew bigger and scarier, and I also wanted to see if I could make an all-Rogue party. These guys were the results, I actually went and fleshed them all out, spec-ing them out and it actually works really well.

Have a jewel heist. Someone needs to be Mr. Pink

[FaceofBo]

Have a jewel heist. Someone needs to be Mr. Pink

Also, fun thing, I also named them all after color, stop reading my mind! lol, jk.
But for real, I've got Red, the Dwarf Mastermind, enforcer kinda guy, with bonuses to Intimidation, and Athletics, plus the grappler feat. Blue, the Kenku Thief, with big bonuses to deception and forgery, he's the intel guy, gets in grabs the intel, and copies it down perfectly. Green, the Gnome Trickster with that passive perception of 20, he's the lookout, and also Blues assistant in theft, he generally grabs the gems and such. White, the Tabaxi Swashbuckler, or the distraction/frontliner number 2, he can pull large crowds with his knife juggling and sword swallowing, as well as blazing feats of speed, so his compatriots have an easier time sneaking around. Finally Grey, the Halfling Assassin, he sits up high with his crossbow and the Skulker feat and rains down pinpoint shot after pinpoint shot to decimate unaware enemies, or to offer assistance to his more thieving fellows.

[Arkhios]

Drop the Assassin and add Mastermind, Enforcer can be a Inquisitor Inquisitive rogue.

Tsk tsk, fixed it for you. Inquisitor and Inquisitive are quite different things.

[Mortis_Elrod]

Tsk tsk, fixed it for you. Inquisitor and Inquisitive are quite different things.

I know what i said. Either would work. I'd rather play your homebrew than the inquisitive ua rogue, yours is very good.

[Arkhios]

I know what i said. Either would work. I'd rather play your homebrew than the inquisitive ua rogue, yours is very good.

Haha, okay. Thanks, by the way :)