Does This Work?

[Expected]

In a campaign I am currently in, I am playing a ranged High Elf Arcane Trickster Rogue. Before I invest too much into a theoretical build, I wanted to seek advice to see if my strategy is viable.

I'd be wielding a Longbow and will have Elven Accuracy and Sharpshooter (the triple advantage will offset the -5 to hit). To generate the advantage to trigger Elven Accuracy, I will have proficiency and expertise in Stealth and will use my bonus action/Cunning Action to Hide and then use the Attack action. I can also utilize Find Familiar:Owl for the times when this strategy cannot work (e.g. in a well-lit open area with nothing to obstruct myself with). This is not essential and more of a bonus of being an AT, but at higher levels, I can cast Haste and hold my action for offturn Sneak Attacks with my Owl granting advantage for that attack.

Now, by RAW/RAI will this work? If not what can I do to generate advantage for myself (getting it from allies is easy and unreliable between campaigns/AL)? And is there anything I can do to further optimize?

[Wildarm]

Yes both hide action and help action can give you advantage. Should be fine. Be careful with sharpshooter on a rogue. You only get 1 attack for the most part and your sneak attack damage will skew the math at which it is optimal to take the -5 to hit. Check the DPR calculator to work out what AC you should be taking the penalty at.

[Keravath]

The only problem with the strategy is sharpshooter and sneak attack.

In order to do the most damage, the rogue wants to hit every turn with advantage so that they can land sneak attack.

Triple advantage is great and optimizing your chances to hit. However, -5 from sharpshooter is a big negative. The initial reaction is to say that it will be compensated for by advantage but look at the numbers.

E.g. tier 2, +3 proficiency, +4 stat - +7 to hit.

Fire at an AC17 target - needs a 10+ to hit.

This gives you about a 91% chance to hit with triple advantage.

However, now apply the -5 for sharpshooter. You need to roll a 15+ to hit and the odds of hitting with triple advantage become 66%.

So which does the most damage? Earliest you can have both feats is level 8.

damage with sneak = d8 + 4d6 = 18.5 (average) * 0.91 = 16.8
damage with sneak and sharpshooter = d8+4d6+10 = 28.5 (average) * 0.66 = 18.81

In this case, you average about 2 points of damage more/round using sharpshooter but you will still miss entirely 1/3 of the time compared to 1/10 without sharpshooter.

If the target AC was 20 instead of 17, the numbers become 13 (78.4%) and 18 (38.6%) which would be an average damage of 14.5 and 11.0 respectively making firing without sharpshooter the better choice.

Sharpshooter is still a great feat for avoiding cover and extending the effective range of weapons. However, for a rogue where your damage increases by level and the +10 from sharpshooter becomes less significant over time, it can often not be a good choice to use.

I have a rogue multiclass with extra attack where I use sharpshooter after landing the sneak attack and it is a good damage boost in that case but it is less useful on a rogue with just one attack.

[Expected]

The only problem with the strategy is sharpshooter and sneak attack.

In order to do the most damage, the rogue wants to hit every turn with advantage so that they can land sneak attack.

Triple advantage is great and optimizing your chances to hit. However, -5 from sharpshooter is a big negative. The initial reaction is to say that it will be compensated for by advantage but look at the numbers.

E.g. tier 2, +3 proficiency, +4 stat - +7 to hit.

Fire at an AC17 target - needs a 10+ to hit.

This gives you about a 91% chance to hit with triple advantage.

However, now apply the -5 for sharpshooter. You need to roll a 15+ to hit and the odds of hitting with triple advantage become 66%.

So which does the most damage? Earliest you can have both feats is level 8.

damage with sneak = d8 + 4d6 = 18.5 (average) * 0.91 = 16.8
damage with sneak and sharpshooter = d8+4d6+10 = 28.5 (average) * 0.66 = 18.81

In this case, you average about 2 points of damage more/round using sharpshooter but you will still miss entirely 1/3 of the time compared to 1/10 without sharpshooter.

If the target AC was 20 instead of 17, the numbers become 13 (78.4%) and 18 (38.6%) which would be an average damage of 14.5 and 11.0 respectively making firing without sharpshooter the better choice.

Sharpshooter is still a great feat for avoiding cover and extending the effective range of weapons. However, for a rogue where your damage increases by level and the +10 from sharpshooter becomes less significant over time, it can often not be a good choice to use.

I have a rogue multiclass with extra attack where I use sharpshooter after landing the sneak attack and it is a good damage boost in that case but it is less useful on a rogue with just one attack.

Thank you for the detailed explanation on why using the -5/+10 bullet point of Sharpshooter is not worth it. Is it worthwhile to take Sharpshooter if I only use it to ignore 3/4 cover and to extend the longbow's range? And for locations with torches, I had an idea to use prestidigitation to snuff out light sources to create areas where I can hide. Would the Skulker feat benefit my build?

[Damon_Tor]

To generate the advantage to trigger Elven Accuracy, I will have proficiency and expertise in Stealth and will use my bonus action/Cunning Action to Hide and then use the Attack action.

There is some debate about this.

There are some who believe that once an enemy is aware of your presence hiding from them is virtually impossible.

To be clear, they are a minority, and I think they're pretty clearly wrong, but they exist and if your DM falls into this category you're going to have a bad time.

[Mjolnirbear]

There is some debate about this.

There are some who believe that once an enemy is aware of your presence hiding from them is virtually impossible.

To be clear, they are a minority, and I think they're pretty clearly wrong, but they exist and if your DM falls into this category you're going to have a bad time.

I don't know about minority, and I think you're just as wrong.

However, your post is very relèvent if for no reason than to point out the issue is controversial and we don't know where OP's DM will fall on the issue. Because of that, it is a good idea to have a backup plan to generate advantage in case OP's DM nukes the hide plan.

Basically, no one here can tell you if it will work; only your DM can.

[ShikomeKidoMi]

If the target AC was 20 instead of 17, the numbers become 13 (78.4%) and 18 (38.6%) which would be an average damage of 14.5 and 11.0 respectively making firing without sharpshooter the better choice.

It's worth noting that a lot of opponents at level 8 do have still have AC 17 or less.


Now, by RAW/RAI will this work? If not what can I do to generate advantage for myself (getting it from allies is easy and unreliable between campaigns/AL)? And is there anything I can do to further optimize?
Hide is going to depend on your DM and the terrain, but don't forget you also have spells as an Arcane Trickster. There are lots of those that will get you advantage on attacks, if you can't rely on your allies.

[Aidamis]

I like the idea but personally I would rather go Rogue for 3 levels (Arcane Trickster), then go Fighter Eldritch Knight (with Archery as my Fighting Style) if I still wanted the magic. You won't get the CON saves or the heavy armor, but you'll get three attacks by level 14 while still retaining stealth/ambush potential.

However, your original concept has still many advantages such as no class features delays, no spell delays and a clear idea of what you're aiming for.

[Randomthom]

I like the idea but personally I would rather go Rogue for 3 levels (Arcane Trickster), then go Fighter Eldritch Knight (with Archery as my Fighting Style) if I still wanted the magic. You won't get the CON saves or the heavy armor, but you'll get three attacks by level 14 while still retaining stealth/ambush potential.

However, your original concept has still many advantages such as no class features delays, no spell delays and a clear idea of what you're aiming for.

If you're going down the ranged sneak attacker, crossbow master with a hand crossbow is better than sharpshooter. 2 attacks = 2 chances to land sneak attack.

If you'd rather go down the bow/sharpshooter route then you're better off as a fighter for the extra attacks (and extra ASIs for earlier access to the feats).

If you need both then Aidamis' suggestion is solid.

If your DM sticks to the concept of the 6-8 encounter adventuring day then Arcane Archer is also worth a look.

[da newt]

A one lvl dip into fighter for the archery fighting style (+2 to hit) and second wind are worth looking into too.

[Expected]

A one lvl dip into fighter for the archery fighting style (+2 to hit) and second wind are worth looking into too.

That is exactly my plan. Stroke of Luck isn't worth it. The +2 to hit will help to further offset Sharpshooter should I choose to use it.

[Aidamis]

A one lvl dip into fighter for the archery fighting style (+2 to hit) and second wind are worth looking into too.

Yup, I forgot for a minute how efficient the one level Fighter dip was. If Rogue is what OP intends to be his primary class, then the dip is a good "economy" pick as far as spell asi and abilities delays go. Thank you for your insight.