D&D 5E How do I optimize this character?

Esker

Hero
Are you suggesting that it’s never worth getting a +2 to hit? Even when willingly taking a -5 (a net +2 with a 20 DEX) to hit?

No, not suggesting it's never worth it, just that from a strictly average DPR perspective, it's perhaps not worth taking at level 10 instead of crossbow expert and advancing your rogue levels, even if you get to take sharpshooter immediately after. Though that's with the large caveat that the above analysis assumes you can almost always be in range and get owl help.

In any case, once you have crossbow expert it likely is a good investment, though I will have to run the numbers to say whether archery style or sharpshooter is better taken next (my intuition is sharpshooter). I'll follow up later.
 

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Esker

Hero
Following up... Let's look at level 12.

Now there are three paths to compare, all of which have 20 DEX and elven accuracy, and again assuming owlvantage on the first attack.

1. Rogue 12 with XBow Expert and Sharpshooter, using a hand crossbow
2. Rogue 11 / Fighter 1 with Archery Style and Sharpshooter, using a longbow
3. Rogue 11 / Fighter 1 with Archery Style and XBow Expert, using a hand crossbow

Here's the average DPR by enemy AC for each build (listed as 1/2/3):

AC 14: 50.9 / 42.4 / 40.8
AC 15: 48.9 / 41.5 / 40.4
AC 16: 46.7 / 40.4 / 39.9
AC 17: 44.1 / 39.1 / 39.3
AC 18: 41.2*/ 37.4 / 38.7
AC 19: 38.6*/ 35.4 / 38.1
AC 20: 35.6*/ 33.0 / 37.3

* At these ACs damage is calculated assuming sharpshooter power attack only on the first attack when you have advantage, then switch to a regular attack for the second one, which is higher than using power attack on both attacks.

So we see that the synergy between sharpshooter and crossbow expert kicks ass, handily outpacing either one combined with archery style except at ACs of 20 and above, when you're best off pouring everything into chances to hit (i.e., combo-ing xbow expert and archery style, which gives you by far the slowest degradation in expected damage as enemies get harder to hit). Except that even there, sharpshooter removes the close range limitation of crossbow expert, and so you'd probably still rather have those two.

Crossbow expert and sharpshooter just complement each other so well, especially for a rogue: the extra attack helps you land at least one attack (and thus sneak attack), making the high risk-high reward proposition of the sharpshooter power attack both that much more viable and more valuable, since you can potentially benefit twice from the +10.

But, after level 12 when you've maxed your DEX, picked up elven accuracy, crossbow expert, and sharpshooter, and picked up the best rogue abilities (cunning action, uncanny dodge, evasion, magical ambush, reliable talent), if your goal continues to be making yourself the best archer you can be, now it would be worth looking at going fighter... except that now you're only one level away from being able to learn Haste, and tacking on yet another attack. For fights when you can have Haste up, it takes an AC of 23 or better for you to prefer having the +2 from archery style. Now, you only have two spell slots for haste, and you may not even want to devote your concentration to that; maybe you're using it for some nice debuff that you used magical ambush to make stick... except you can also learn Hypnotic Pattern at level 13, and if you can hide, impose disadvantage on the save. So... maybe you still don't want to take that fighter level yet.

If you're going to be a haste archer for the rest of your days you might as well start taking fighter levels after level 13, as by level 18, extra attack is worth more to you damage-wise than the sneak attack dice you miss out on, plus getting battlemaster maneuvers gives you precision attack to help cover the times when you would have missed. Alternatively you could go bladesinger to boost your spell slots and spells known, leaning into that sweet sweet magical ambush, and still get extra attack for your last couple of levels. Since you're using a hand crossbow you can still use bladesong (some DMs might disagree based on the interpretation of the phrase "use two hands to make an attack with a weapon", since you do need that other hand to load it? but seems fine to me).
 

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