I don't quite know where to post this but I'd thought I would give it a shot here and see what people are thinking to this question.
Question:
If you have Brawler's flurry (Or two weapon fighting) and have the respected feats of such as Upsetting shield style (including even Unhindering shield feat) and weld both of them in one hand.
Could you Shield bash with the arm, then alternate to the weapon that is being held with the strapped Buckler with attacks after or vice versa?
So some context:
I was making a character that has Brawler's flurry and his main thing was going to be welding a weapon to flurry with while having a buckler in his off hand to provide some utility and defense. Namely going down the upsetting shield style line and stumbling bash feats etc.
After I created the concept and put it on paper I was satisfied, but another thought occurred to me if it was possible to go further with it.
You cannot shield bash with a Tower shield but I was thinking more defensive AC for my character would fit the theme and then the idea dawned on me.
What if he welded a Tower shield in his off hand, but strapped a buckler in his main hand and also drew his main weapon as well.
Effectively he would hold his weapon and a buckler (since the buckler can be shield bashed with due to feats) in his main-hand and have a tower shield in the off-hand which is effectively a dead hand like normal since you cannot weld or manipulate anything while using it.
I'm well aware shield bonuses do not stack because of the tower shield and buckler and that there is an additional -1 penalty to the arm with the buckler for attack rolls involving using it with a weapon. (TWF -2 plus the -1 buckler penalty totaling -3)
But all the threads I've scoured involved twf and whether or not you could shield bash with the buckler or something to the degree with two-handing weapons or using it with bows.
This is a unique question I wanted to ask that I had issues in finding with my search-fu.
I would say yes with Brawler’s Flurry, no with conventional two weapon fighting. With the caveat that you need to be able to Brawler’s Flurry with a buckler in the first place, which I don’t think is a given.
Upsetting Shield Style allows you to treat the buckler as a light shield for feats and abilities, so it should work.
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The TWF rules are referring to "metaphorical hands", not literal hands. You could definitely Flurry/TWF with your buckler and a weapon held with the same arm, in the same way you could TWF with armor spikes and a longsword.
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Edit:
Do keep in mind that if you're using Weapon Finesse, you'd add your Tower Shield's ACP as a penalty to your attack rolls. Even though you're proficient with it.
With a light weapon, elven curve blade, rapier, whip, or spiked chain made for a creature of your size category, you may use your Dexterity modifier instead of your Strength modifier on attack rolls. If you carry a shield, its armor check penalty applies to your attack rolls.
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Starting at 2nd level, a brawler can make a brawler’s flurry as a full-attack action. When doing so, a brawler has the Two-Weapon Fighting feat when attacking with any combination of unarmed strikes, weapons from the close fighter weapon group, or weapons with the “monk” special feature. She does not need to use two different weapons to use this ability.
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You can shield bash with a buckler as if it were a light shield, and you can use the buckler in conjunction with any feats or abilities that normally apply to light shields.