Flurrying with a hooked boss buckler

[Mechanical Pear]

If a monk has buckler proficiency, and the unhindering shield feat, can he exchange one attack with a trip combat maneuver using the hooked boss buckler?

You're not making an attack with the buckler; you're using a combat maneuver in place of an attack. So I dunno.

And if this monk can do this, is there any raw about using his Dex for his bonus, as he would be able to with, say, a dagger?

And do I keep my buckler AC even when I try to snag people with it?

[Mechanical Pear]

Also, if this monk has three levels of swashbuckler, would this count as "attacking with another weapon in the other hand" for precise strike?

[Azothath]

[not PFS]Unhindering Shield feat check the requirements... free hand/off-hand affect some classes. Special exception & limited cases for monk. [not PFS] lets you know there are likely issues. #1) handedness debates always draw a lot of controversy with no happy resolution. #2) -1 atk and losing AC bonus are overcome in 1 feat without action tax of "shouldering" shield(quickdraw shield and quickdraw feat). #3) the monk exceptions are added gravy that is self-contradictory (when is an AC bonus not an AC bonus?).
The core issue is that this feat effectively moves an enhc shld AC bonus to always on where you "get it all", why not wear two?!

shield bosses hooked boss lets you make trip attempts with shield to cause foe to become flat-footed. Applicable upgrade to buckler.

You can make a CM attempt for an attack but provoke before the attack without further feats, see special attacks.

Unfortunately "boss" is not on the weapon list nor any text to that effect, unlike a shield spike, so it's not a weapon. No Weapon Finesse. The hooked boss runs of CM so I'd ask if your CMB runs off Dex???
The shield can do a shield bash (w or wo the boss).

Unhindering Shield Feat users keep the buckler AC due to the shield boss falling under "other purpose".

[Azothath]

Azothath wrote:

...

You can make a CM attempt for an attack but provoke before the attack without further feats, see special attacks.
...

{since you mentioned "Flurry" in your title}

IUS & Flurry are a bit different than a standard attack or std atk action.
CRB A monk may substitute disarm, sunder, and trip combat maneuvers for unarmed attacks as part of a flurry of blows. One assumes the penalties follow through with the CMB attack.

[Mechanical Pear]

If you can trip during a flurry, then you use strength or dex for your bonus, depending on weapon finesse and such (not on all combat maneuvers, but trip is one).

I have weapon finesse. Even though I'm using the buckler, would it still count as the unarmed strike that the maneuver replaces, and be based off dex?

Or, since it's unspecified, does it go to the default strength?

[Azothath]

Mechanical Pear wrote:

If you can trip during a flurry, then you use strength or dex for your bonus, depending on weapon finesse and such (not on all combat maneuvers, but trip is one).

1) I have weapon finesse. Even though I'm using the buckler, would it still count as the unarmed strike that the maneuver replaces, and be based off dex?

Or, since it's unspecified, does it go to the default strength?

1) no, trip runs off CMB not your 'to hit'/attack with Improved Unarmed Strike(IUS). If you replace a flurry it gets the flurry penalty.

Weapon Finesse feat for lgt wpns, a few others, and natural attacks you may use your Dexterity modifier instead of your Strength modifier on attack rolls. IUS(and thus Flurry) is an attack but not specifically called out.
Applicable FAQ clarifies you must use a finessable weapon with the CMB. Since the shield boss is not a weapon... no. (I did say there would be problems) Readers are directed to Agile Maneuvers feat.
The corollary is that you must use a finessable weapon with IUS(& flurry).

Without Improved Trip feat the attempt to trip provokes.

Only your Home GM can resolve the issue. My suggestion is just to ban the feat. You could call the shield boss a finessable weapon but the feat needs to address the issues in my first post.
Part of the issue is shield mwk at $150 and enhancements affect AC not attacks. A shield needs a spike(weapon), mwk $300, and then separate weapon attack enhancements to affect +atk(+dmg).