It was a process. And I was looking at other churches at the same time.
Some things were easy - like "call no man Father" ... simple enough to understand what the original language is saying, and the fact that Paul calls himself Timothy's father, and so on.
Baptismal regeneration was one of the more difficult. The problem was, nearly every other church I was interested in believed it too. So I really had to deal with that one early on.
First, I had to accept the fact that I could be wrong about something. I set out to find out what was the TRUTH - and in that process I had to accept the painful fact of such things as having been taught easy-believism ... yet here was Paul talking about running the race, being afraid of being disqualified, buffeting his body so that he might be saved. So basically I decided to dump everything I had been taught, start from square one, and try to find the truth, no matter how distasteful to me it might be.
When I read the Scriptures with NO preconceptions, I had to admit that it could be there. I couldn't prove one way or another. Reading the ECFs helped cement what the early Church believed though. And when I read the Scriptures through their lens rather than my own, I saw a completely different story, and finally (almost regretfully) had to accept it.
From there, I began working through everything one at a time. Some it was a sudden insight because of words someone said to me, or I came to understand better because of prayer. Some was easier to prove in Scripture. What helped me a lot was to slowly develop a "whole mindset" kind of approach. This was NOT easy for me. There is such a huge difference in the way Orthodox will approach a question. But as I came - very slowly - to understand how it all fit together, it started making tremendous sense. It is as though I had been looking at a tapestry from the back, and it wasn't until I took a completely new look from a new direction (the front) that I realized that all those threads DID fit together to make a story of mankind and God, the Fall and Salvation, and everything. The key to these things for me was having a better understanding of the theories of Atonement, and shifting my focus from simple penal substitution to seeing the whole thing from creation to the eschaton as a continuous purpose of a LOVING God. I'm not sure if that makes sense or not. But I couldn't have gotten there by only seeing little pieces. In our Church, Father often says that we must view all of Scripture through the Gospel, and that is a good description of this process for me. The God of the OT can be very confusing - unless you know Christ and can see it all through that context.
That didn't solve all of my problems. To be honest, even when I was baptized, I still had some lingering issues I had not perfectly solved to my satisfaction, about the Theotokos. But what I did there was to look at my whole situation. I had found the Church to be correct in the end, with everything I investigated. Historically they have a huge advantage over me - they have held all this knowledge and dealt with it for 20 centuries. I came along a handful of decades ago, and I have to believe what I read about history, faith, and everything else, and make the best logical decision I can. But I don't have what they have. I also had to basically chose to submit in those areas. I don't do things I'm not comfortable with or don't understand, but I decided to put my reservations in a place that I just labeled "I will submit to the Church". I can't very well start my own Church - I'd get plenty of things wrong. I want to be part of a Church, and right now I feel that's the right thing according to Christ's command, and the Orthodox Church was by far my best choice. The others I considered had major theology or mindset errors, imo.
And to be honest, I think God has honored my choice. Certain of those issues I now understand (the simplest of them were just semantics) and others I have begun to understand for other reasons. There are one or two minor things I still put aside, and submit for the purpose of obedience to God to belong to a Church and receive the Eucharist. Those points are not things that bear on salvation anyway. And jurisdictional issues, or those that vary due to economia - are not things to keep myself out of the Church over. I have reasons for that too.
I have been given so much help through the Church for my Christian walk, and I am thankful that this is what I have decided. As time goes by, I see more and more indication that it was the right thing to do. No Church is perfect when you consider the people that make it up, but what I get from the Orthodox Church is perfect.
Sorry, I have no idea if you wanted to know all of that. It seemed the best answer. I can address particular issues if you like, but the process seemed the important thing.
God be with you. (And I'm sorry this is so long!)