Pen and Sword in Accord

There's a lot here I agree with. Especially:

As much as I try and present a story for the players to help flesh out though, I keep in mind that this is a game. In all but the most extreme circumstances, I let the dice "fall as they may", and try not to twist the rules simply to accommodate my story idea.

As it turns out, I think letting the dice fall where they may makes for a stronger story experience. One of the challenges for writers of fantastical fiction is making the world and characters feel real enough for the readers to invest in (aka verisimilitude). When writers talk about creating and preserving verisimilitude, they actually use phrases like: "Your world must be consistent; don't break its internal rules!"

When you fudge a die roll or pretend, "Well, ok, that will work this time," you're damaging your verisimilitude. You're weakening your story. (Likewise, when you whip out your story points to change the rules temporarily, you're weakening verisimilitude unless those story points have actual existence within the world of your story. This is why I can't enjoy most story games; they actually have mechanics in them that damage the story!)

But when you apply the rules of your game consistently, you strengthen the verisimilitude and you make the story more enjoyable. When players know how their magic works, or how likely they are to defeat a troll, or how the city guard will react when they discover a pick-pocket, they can invest emotionally in their characters and the world they inhabit.

In short, if you want your RPG sessions to have the effect of a story (rather than just mimic the structure of a story), you need clear, understandable, and consistent rules. (It’s not all you need, but without them you’re not even going to get started). This is also why it’s important that the rules you choose actually promote the sort of story you want to tell. If you’re fighting your rules, you’ll constantly see your story drift away from the look-and-feel you were aiming for.

5ogues

I recently had a chat with a friend who’s running 5e for the first time after pretty much sticking with 2e since the ‘90s. One of his players was playing a rogue, and he wasn’t sure what made that class unique in 5e.

Confusion is understandable, because in many ways, the 5e rogue is the antithesis of the 2e thief. 2e’s thief was often found far ahead of the party, using their stealth and trap-detection abilities to scout out what was around the corner or further down the corridor (or listening to discern what was on the other side of the door) before reporting back to the rest of the group. In a fight, they were either a bodyguard for the magic-user or were sneaking around the edge of the fight, looking to get in a backstab on the enemy spell-slingers, snag the Magoffin, or unleash a nasty alpha-strike on a boss monster. After unleashing their backstab, however, they were a second-rate fighter-type with poor hit points and inadequate armor; they primarily survived because, after unleashing the back-stab, they were not much of a threat to anyone.

Most of the special abilities of the 2e thief are now possible by anyone. Listening at doors is a Perception check; the cleric is likely to be really good at it due to their high Wisdom. Ditto searching for traps. There are a few backgrounds (including Urchin) that grant proficiency with thieves’ tools. Stealth is now something anyone with high Dexterity (and less-than-heavy armor) can pull off, so there’s no reason for the rogue to risk going alone to scout.

In fact, the last thing the 5e rogue wants to do is be caught out by themselves. Their back-stab ability can be invoked anytime they’ve either got advantage or their target has another foe in melee range. So what the 5e rogue really wants to do is back-up frontline fighters and clerics. And they’re really good at this because their Cunning Action ability allows them to get extra movement, or attack and then disengage safely the same round.

This means the 5e rogue makes a great mobile reserve. They can move in against a foe already engaged to ensure flanking bonus or just to deal out extra damage. Or they can rush in to support a character who’s hard-pressed by the enemy. They can support a cleric who needs to take a round to cast healing spells rather than fight.

They could use that extra movement to harass enemy spell-slingers or snag Magoffins, but they’re far less effective combatants when they can’t use their sneak-attack bonus damage. (Besides, the barbarian and druid are both much better at the deep-penetration of the enemy backfield.) They can put together some powerful synergies, for instance by fighting alongside a druid transformed into a wolf (who gains advantage thanks to Pack Tactics), a paladin with Aura of Protection, or a fighter with Commander’s Strike or Rally. And at mid-level, a rogue is able to stay in the fight longer thanks to Uncanny Dodge and Evasion.

5e’s rogue is not the antisocial loner 2e’s thief was. They’re a support-class, rather like the cleric and the bard, but unlike those, they don’t buff their allies but rather get buffed by being close to their allies. A 5e rogue should buddy-up with a character who’s either putting out a lot of damage or can create synergies with the rogue’s sneak-attack bonus damage. And they should stay mobile throughout the fight, ready to hop over to another part of the battlefield to aid someone else.

Outside of fights, they’ll probably find use for their thieves’ tools, but they might not be the only one who’s got them, nor are they necessarily the best at sneaking or perceiving dangers. This does allow the rogue to be much more flexible, concentrating on any holes the party has in their skills. This can be especially useful in a party that doesn’t include a bard.