Setting rotations on equipable items: Cannot match rotation to parent bone

In a nutshell, I have a nested array of bones that handle my main character. I am trying to attach equip-able items which have only one bone.
My problem is that, while I can attach said item to the bone I want, if I try to make a rotation correction (right after I .add the equipment bone to the parent bone I want since if I do it before those transformations seem to disappear) so that the item is held in the right position, it does everything but what I need it to. Tried using getWorldDirection on the parent bone, tried doing worldToLocal and localToWorld shennanigans but to no avail. Honestly I have no Idea how to fix this.
On the same note, I also have a problem regarding rotations but its regarding the Camera. If I try to make a camera LookAt an object, it does but it does not change its orientation to match the object. For example, if the camera is vertical and the object is horizontal with text, if i LookAt it the camera doesnt go sideways. This is problematic as I have an object that is constantly changing directions and, at some times, i need the camera to pan to it.

I’d greatly appreciate any help! Thank you

Example of character holding with no rotations (the child and parent bone share position and rotation)