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If a Signifer made his bonded item a mask and enchanted it as a Mask of a Thousand Tomes, would the mask blind him? Both masks don't have eyeholes. The real question is, is the blinding effect of the Mask of a Thousand Tomes due to not being able to see through it, or is it a magical effect? If the effect is non-magical, a Signifer should be able to wear it permanently with the ability to see through it.
Argument for the effect being non-magical: It is an eyeless mask that inhibits sight whilst worn - any non-magical mask does that. There is also nothing like "Cause Blindness" as a spell requirement.
Argument for the effect being magical: It is a magical item that says it blinds you whilst worn, therefore a magical effect.
Crafting requirements: Craft Wondrous Item, clairaudience/clairvoyance
A Hellknight signifer with a bonded object from the arcane bond class feature can perform a special ritual that costs 500 gp and takes 8 hours to complete. This ritual converts the signifer’s mask into his new bonded item, which takes up the head slot. In this case, Hellknight
signifer levels stack with levels from the class that grants the bonded item for determining what additional magical abilities can be added to the bonded item.

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The Mask itself doesn't obscure the signifier's vision. Unfortunately, the Mask of a Thousand Tomes gives the wearer the blinded condition.
So the mask isn't blocking the vision of the Signifier, but the signifier is blind so it's irrelevant anyhow.
It is very relevant. If the blindness is due to the mask acting like a blindfold because of no eyeholes, the signifer's mask would see through it as a signifer's mask is enchanted to see "through" the mask.
If, however, it is a magical effect related to gaining the +10 skill bonus (such as a virtual reality effect), then the Signifer would still be blind.

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Since the blindness isn't stated as coming from the mask acting like a blindfold, it's not coming from the mask acting like a blindfold.
As written, the mask afflicts the wearer with blindness, as opposed to merely blocking their vision completely (which would be obscurement). So the signifier would have a mask that gave them the blinded condition even if they had two sets of eyes and only one set was covered.