Generally speaking, does dual wielding stop being useful at higher levels, due to having more/better options for your Bonus Action? Does that happen at all? Across the board? To some classes/subclasses, but not others?
It's certainly class and subclass specific as they vary greatly in what bonus options they get. For example Berserker Barbarians already get a normal attack as their bonus action whenever they are in a frenzy rage. Clerics and druids tend to use their bonus actions a lot for casting spells, and sorcerers with access to quickened spell as well (plus many spellcasters aren't often going to be in a position to use two light weapons usefully anyway). On the other hand rogues can make great use of it (as you know if you've watched campaign 1 of Critical Role) even though they have many bonus action options, as for a lot of fights their other options aren't as useful as attacking an extra time. Fighters also only really use their bonus action for second wind, with some exceptions like Battle Masters with bonus action maneuvers, and Eldritch Knights that can combo a bonus action attack with spellcasting.
Rogues and monks (with perhaps a side of Rangers) get the most bang from the dual wielding abilities. For the rogue yes you give up using your free disengage and such, but if you missed with your first attack to get sneak attack damage then you have the chance to make a second one, if you make the first hit you can then dance out of range with disengage, and then potentially stealth the next round (if possible) and go right back in to sneak attack again. Monks just live off their dual wielding nature.
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"Where words fail, swords prevail. Where blood is spilled, my cup is filled" -Cartaphilus
"I have found the answer to the meaning of life. You ask me what the answer is? You already know what the answer to life is. You fear it more than the strike of a viper, the ravages of disease, the ire of a lover. The answer is always death. But death is a gentle mistress with a sweet embrace, and you owe her a debt of restitution. Life is not a gift, it is a loan."
I would've thought that monks would prefer using their bonus action for martial arts, especially considering that from lvl 5, it's as good as a short sword, and from lvl 11 it's better than a short sword. Even before level 5, using a Quarterstaff yields better damage (considering the extra martial arts attack) than dual wielding short swords, especially considering the martial arts bonus action gets stat bonus added to damage, while offhand short sword does not.
The effectiveness of two-weapon fighting varies a lot by class and subclass, as others have pointed out. It's very powerful for Rogues, since Sneak Attack quickly eclipses their normal weapon damage, but they normally only get one chance to hit per round. It's also pretty good for Rangers in fights with a small number of tough enemies, since they get to add the damage from Hunter's Mark more times. Non-berserker Barbarians can also benefit from it as well since they get to add their Rage damage to the extra hit if they use Strength.
On the flip side, it's not as good offensively for Fighters that have 3 or 4 attacks, since the extra damage from other weapons starts to add up, and feats like Great Weapon Master or Sharpshooter can let them deal higher damage if they get advantage. Even so, it can be situationally useful if they're trying to interrupt a spellcaster's concentration and want as many chances to hit as possible. Many characters don't make it to level 11+ either, and it's still pretty competitive with other fighting styles up until that point.
You're right about it being borderline useless for monks unless they happen to have really good finesse magic weapons.
My impression of dual wielding has not been favourable, mostly due to the reasons given by those above. I would add that the reason for one extra attack using the bonus action in any case should be judged on whether it is an improvement on using the hand for something else (shield, two handed weapon or spell cast). The few times I have seen it successfully championed were.
Rogues for the sneak attack fail redundancy
Hexblade locks and rangers (using hit boosters hunters mark and hex)
Those who had magic weapons adding dice to their attack (in both hands - not taking into account if someone else in the party might be better off wielding)
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Generally speaking, does dual wielding stop being useful at higher levels, due to having more/better options for your Bonus Action? Does that happen at all? Across the board? To some classes/subclasses, but not others?
It's certainly class and subclass specific as they vary greatly in what bonus options they get. For example Berserker Barbarians already get a normal attack as their bonus action whenever they are in a frenzy rage. Clerics and druids tend to use their bonus actions a lot for casting spells, and sorcerers with access to quickened spell as well (plus many spellcasters aren't often going to be in a position to use two light weapons usefully anyway). On the other hand rogues can make great use of it (as you know if you've watched campaign 1 of Critical Role) even though they have many bonus action options, as for a lot of fights their other options aren't as useful as attacking an extra time. Fighters also only really use their bonus action for second wind, with some exceptions like Battle Masters with bonus action maneuvers, and Eldritch Knights that can combo a bonus action attack with spellcasting.
Rogues and monks (with perhaps a side of Rangers) get the most bang from the dual wielding abilities. For the rogue yes you give up using your free disengage and such, but if you missed with your first attack to get sneak attack damage then you have the chance to make a second one, if you make the first hit you can then dance out of range with disengage, and then potentially stealth the next round (if possible) and go right back in to sneak attack again. Monks just live off their dual wielding nature.
"Where words fail, swords prevail. Where blood is spilled, my cup is filled" -Cartaphilus
"I have found the answer to the meaning of life. You ask me what the answer is? You already know what the answer to life is. You fear it more than the strike of a viper, the ravages of disease, the ire of a lover. The answer is always death. But death is a gentle mistress with a sweet embrace, and you owe her a debt of restitution. Life is not a gift, it is a loan."
I would've thought that monks would prefer using their bonus action for martial arts, especially considering that from lvl 5, it's as good as a short sword, and from lvl 11 it's better than a short sword. Even before level 5, using a Quarterstaff yields better damage (considering the extra martial arts attack) than dual wielding short swords, especially considering the martial arts bonus action gets stat bonus added to damage, while offhand short sword does not.
The effectiveness of two-weapon fighting varies a lot by class and subclass, as others have pointed out. It's very powerful for Rogues, since Sneak Attack quickly eclipses their normal weapon damage, but they normally only get one chance to hit per round. It's also pretty good for Rangers in fights with a small number of tough enemies, since they get to add the damage from Hunter's Mark more times. Non-berserker Barbarians can also benefit from it as well since they get to add their Rage damage to the extra hit if they use Strength.
On the flip side, it's not as good offensively for Fighters that have 3 or 4 attacks, since the extra damage from other weapons starts to add up, and feats like Great Weapon Master or Sharpshooter can let them deal higher damage if they get advantage. Even so, it can be situationally useful if they're trying to interrupt a spellcaster's concentration and want as many chances to hit as possible. Many characters don't make it to level 11+ either, and it's still pretty competitive with other fighting styles up until that point.
You're right about it being borderline useless for monks unless they happen to have really good finesse magic weapons.
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My impression of dual wielding has not been favourable, mostly due to the reasons given by those above. I would add that the reason for one extra attack using the bonus action in any case should be judged on whether it is an improvement on using the hand for something else (shield, two handed weapon or spell cast). The few times I have seen it successfully championed were.
Rogues for the sneak attack fail redundancy
Hexblade locks and rangers (using hit boosters hunters mark and hex)
Those who had magic weapons adding dice to their attack (in both hands - not taking into account if someone else in the party might be better off wielding)