I'll try to help if I can.
I am currently on my journey from Roman Catholicism to British Orthodoxy, and happy to share my thoughts.
I have been RC all my life (I'm in my 60s now!) but recent years have seen me becoming more and more unhappy with the Church that (as Father Simon put it to me) had nurtured me. I spent some time looking around seeking a way forward, even to the extent of looking outside of Christianity. I read Abba Kallistos Ware's book, and realised there was much in Orthodoxy with which I sympathised. Eventually I found Orthodoxy, both Greek and Russian who worship near me, but trawling through Google came up with the BOC. I am perhaps a little more fortunate than you, because I live close to Father Simon, and I was able to contact him easily and discuss matters.
He gave me the DVDs that he has offered you as a starting point. Because I was already Christian there was little I needed to learn from that point of view, but I have a long way to go with my knowledge of Orthodoxy. Under Father Simon's guidance I have attended Divine Liturgy and a local prayer/discussion group. I have come to feel extremely comfortable within the BOC. It is a prayerful place to be, but very loving and welcoming. (Sadly this is apparently not always the case with some other branches of Orthodoxy which are reluctant to accept you if you are not culturally the same as they are. Regrettably much the same can be said of Rome as well. However many are very welcoming, particularly our Coptic brethren.) A few months ago I was accepted as a catechumen, and will probably be Baptised into Orthodoxy in a couple of months.
It is difficult to know exactly what will give you support and encouragement, but if there is anything specific don't hesitate to quiz me on my experiences.
One thought that may help you relates to Salvation. You mention your puzzlement about the distinction between the legalistic Roman view and "whatever the BOC thinks about it" so to speak. Perhaps you would find it helpful not to see Jesus' salvation of us as 'paying for our sins'. Rather, consider that mankind has become ill through rejection of God's way. Just like if you are ill you seek a cure from your doctor, so Jesus provides us with healing. He makes us well again. Being well, we are restored to communion with God - hence salvation. I hope this is not too simplistic - I'm sure Father Simon can, and will, put it much better than I can.
With love and prayers,