Padma
Let's look at Shepherd first. What does a shepherd do? A shepherd herds and tends; therefore, I interpret Shepherd as careful attention to detail and "fine-tooth combing" through situations.
Next, the Eye. Obviously an eye watches and keeps tabs on everything in its sight. So for me, as a card in a position to modify/describe Shepherd, the Eye means being watchful and weary.
So Shepherd + Eye to me might mean watching detail or tending to something literally having to do with one's eye. Depends on the context of your question.
Dancer, I haven't seen Azul Paradiso for a while here (this thread does go back a bit in time) but I think your take is good - regarding Shepherd and Eye - and I believe this deck thread is a good one to reanimate! I also have this deck, but I find it a bit dark to work with. I would welcome a new in-depth look at it through the eyes of other Forumites.
There are other good threads on it, I think DownUnderNZ did a pretty thorough one, if memory serves - but I am glad to see this one come back.
And goodness, but I do miss Cardlady! Her talents for analysis were outstanding....