While I addressed part of your concern in my message, "Learning Orthodoxy", allow me to add (at your invitation) how I came to be at peace with the strange concepts of Mary--Theotokos, Icons and the veneration of both.
First, if you check on this site, there is a great video stream available on icons and iconography. In it you will learn the difference between veneration and worship: we venerate kings and leaders and ancestors and family and dear friends. We give absolute worship only to God.
I still had a hard time having heard this explanation, until I read an Orthodox writer's thoughts: He said that to him, walking into the church and being surrounded by icons is like surrounding oneself with the pages of a family photo album.
Because Orthodoxy believes that when the church VISIBLE gathers, the church INVISIBLE gathers with it, the icons serve as a reminder of a higher spirtitual truth that IS reality.
You've certainly been in a gathering where someone has said, "Gee, I feel like Grandpa is right here with us now" or some such thing. Well, Orthodoxy teaches that all who have gone before us in Christ ARE there with us as we turn our attention as a whole to the altar.
I'll finish with this in a moment, but let me move on to Mary, the blessed Theotokos.
Would you agree that the word Apostle indicates that a person was a witness of the Lord Jesus Christ to the early church?
Then ask yourself this: who was the FIRST Apostle...you are correct if you say Mary. Who else but the handmaiden of God, The Mother of The Incarnate God could witness to the world of the truth of his divine origins?
Finally (to tie it all together) if you were my friend, and you offended me in some way, and you felt unworthy to come to me and ask for my forgiveness, would you not perhaps approach one of our mutual friends to say a word to me on your behalf?
And if the intervention of a mutual friend might work, how much more help would the intervention of MY MOTHER be?
When we venerate Mary and the Saints, it is because we know through faith that they are friends of our Lord and Saviour. We are simply reaching out through friends to our Greatest Friend, Jesus Christ.
And Mary led the way for all of us, for in accepting the will of God and allowing herself to be the Mother of Jesus, she pointed the way for the church, for she was the first to subjugate herself to the indwelling of God.
For this reason (and I'm sure others that can be taught) Mary is venerated as the Blessed Theotokos.
I hope this helps you. I also hope I have not misled you in any way. If I have, I ask God's and your forgiveness.
In the name of The Father and of The Son and of The Holy Spirit,
Gordius Ignatius