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The cheese is strong with this. First off Bladesong ends if you use 2 hands to make an attack with a weapon, I would say that having a weapon in each hand breaks the spirit of this, even if it does not breaks the wording and I would rule it out as cheese. Other tables may vary.

Second, heavy obscuration, according to the PHB (page 183) confers the blindness condition to creatures within. So attacks on you are at disadvantage but so are your attacks on them. Alertness does not really help at all. In my opinion it would need the Blind Fighting style from Tasha's picked up as a feat to make this work.

Obscuration as a tactic is going to upset the rest of the party unless the whole lot are set up for blind fighting. I could see that one annoying the DM though.

If you want permanent disadvantage on attack roll to you get a cloak of displacement or figure out some way for a third party to cast blur on you, or greater invisibility.

The spell selection is interesting though. I could see some eyebrows raised if one visits the local hostelry with a greater demon in tow.

I am also not sure Rope trick works like you imply. My understanding is that once cast, one has to climb the rope to get in, so 60 feet of rope, 2 turns climbing, unless one as a climb speed of 30 feet.
It is kist the second rapier at level 1 to 5 that is impossible. Alertness and blind fighting style both have their merits. I would also tend to take blind fighting, but that is really a taste thing.

The Idea of darkness + devil sight is not new. Its also no news that it annoys the rest of the party. But on the other hand, if there is no spellcaster relying on line of sight, attacks are neither have disadvantage nor advantage. So for most character, nothing changes. A rogue might be annoyed, because I am not sure right now, if the cancellation of advantage is enough to be able to sneak attack, but here chosing blind fighting style might grant them a lot of benefits.
 

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It is kist the second rapier at level 1 to 5 that is impossible. Alertness and blind fighting style both have their merits. I would also tend to take blind fighting, but that is really a taste thing.

The Idea of darkness + devil sight is not new. Its also no news that it annoys the rest of the party. But on the other hand, if there is no spellcaster relying on line of sight, attacks are neither have disadvantage nor advantage. So for most character, nothing changes. A rogue might be annoyed, because I am not sure right now, if the cancellation of advantage is enough to be able to sneak attack, but here chosing blind fighting style might grant them a lot of benefits.
Yes, definitely messed up my A+ on the rapier thing, gotta be Shortswords or Scimitars sob

I would hope the Rogue appreciates a constant field of obscurement to Hide in!

But yeah, you gotta work it out with your party. Ideally everyone optimizes for Heavy Obscurement but if someone insists on a Conquest Paladin or something, I'd go in another direction.
 

NotAYakk

Legend
The cheese is strong with this. First off Bladesong ends if you use 2 hands to make an attack with a weapon, I would say that having a weapon in each hand breaks the spirit of this, even if it does not breaks the wording and I would rule it out as cheese. Other tables may vary.
No, two-weapon bladesingers fit the rules, fit the spirit, and are intended by the rules.

You just aren't supposed to use a great weapon, a versatile weapon in 2 hands, or a bow/crossbow.
 


No, two-weapon bladesingers fit the rules, fit the spirit, and are intended by the rules.

Fit the rules? It can be interpreted that way, but "[Bladesong] ends early if [...] you use two hands to make an attack with a weapon," is extremely ambiguous phrasing. It could mean that it ends if you attack with a two handed weapon or with a versatile weapon, but that's not the only interpretation here.

Fit the spirit and intent? Eh... I think it's a huge leap to say that you know the mind of the author. Presumably when they wrote the class, they read through what the class did previously. Is TWF consistent with the class historically?

From the 2e Complete Book of Elves:
Bladesingers rarely use weapons other than swords. With only rare exceptions, they never learn two-handed fighting styles. They may not use shields or two-handed weapons, for these interfere with the bladesong. Even when they have run out of spells, Bladesingers will fight one-handed or with both hands on their single-handed weapon. To do otherwise negates all bladesinging bonuses.


From the 3e Tome & Blood:
Bladesong Style: When wielding a longsword in one hand (and nothing in the other), the bladesinger gains a dodge bonus to AC equal to his Intelligence modifier.


3.5e Complete Warrior's Bladesinger uses the same language, and the additional features Song of Celerity and Song of Fury both include the same "when wielding a longsword in one hand (and nothing in the other)" language.

So, is TWF consistent with the class historically? No. Not at all.

However, even if you allow TWF, it's not exactly a good idea to do it. 5e still requires that spellcasters have a hand free to cast any spell with a somatic component, and that includes both booming blade and green-flame blade. It also includes shield, absorb elements, and counterspell. Even if your DM allows TWF, doing so basically eliminates your ability to cast spells. Welcome to fightertown!
 

NotAYakk

Legend
TWF never uses two hands to make an attack with a weapon. I get dverything is ambiguous, this is English, but there isn't a mechanical/balance issue (the character even needs warcaster, or needs to drop a lot of daggers).

Even in the quotes, bladesingers uncommonly used two weapons. One consistent thing was never a 2 handed weapon (one version permitted 2 handed longswording).

But more power to you if you want bladesong to disappear the moment the 2nd hand ever makes an attack with a weapon (not, of course, from having it equipped).
 
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It would have been very easy to phrase the text to prevent duel wilding if that was the intent: "you must have a hand free in order to use bladesong". That it was instead phrased so as to only forbid shields and two handed weapons implies the intent was to allow duel wielding.

Also, Movie-Gandalf needs his duel wielding staff and sword cheese.
 

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