Will I get the feat bonus if I am using both hands to wield a two-handed weapon and having the Winged Shield float near me?
The feat:
Shield Specialization
Benefit: You gain a +1 feat bonus to AC and Reflex when using a shield with which you are proficient.
And the item:
Winged Shield
Property: You do not need to use your shield hand to gain the shield’s bonus to AC and Reflex; it floats about within your reach as if you wielded it. You can use your shield hand to hold another item, climb, wield a weapon, make attacks and so on. If you have a free hand, you may count as wielding a shield as a free action. Attempts to take away the shield are resolved as if you wielded it normally.