Black, White, or Gray?

Until my 20s, my theological stance was very black and white. I could state with conviction where I stood on issues, and unequivocally state that anyone who thought differently was wrong. However, I was also limited in my exposure to other points of view. As a child and teen, any exposure to an opposing view was given in context of how to argue against that viewpoint. Doubting and questioning were discouraged and viewed with suspicion.
While there are instances in which a person's doubts and questions have led them astray, I do not think that such a thing is always the case. For the past five years, I have found myself wondering why I believe what I believe, and whether or not my belief is the only "right" way to believe about an area. Certainly there are some things that are not up for debate, such as the nature of God and the identity of Christ. But in other areas, is there actually a "right" point of view, or is it a matter of preference?
The ones I have met that hold different views quite often appear to be following the dictates of their own conscience. When I have taken the time to read about their point of view, I often find that I cannot discredit their point of view. I might not switch over to their viewpoint, but neither can I clearly state that it is absolutely wrong.
My increased willingness to accept other views as valid has given me cause for concern. On one hand, I would like to think that as I mature, I am becoming less judgmental, more loving towards others. Yet on the other hand, I fear that I am merely becoming more lax in my faith and less willing to call things out for what they are. Admonishments against the easy path, the wide gate, fence sitting, or becoming lukewarm ring in my head with the voices from my childhood. Voices of people that I respect.
I want the love of Jesus to be the guiding principle of my life, not legalism.
I know to search the Scripture when I have a question about an issue, yet in so many cases, two people can read the same verse and come away with differing views. Also, not every issue is addressed in Scripture. Sometimes the verses used to support a point of view have been taken out of context. So unless one view clearly contradicts something clearly stated in Scripture, how do I know which view is true? Does it (and I mean no disrespect) actually matter which view is right when it comes to some issues? Is there truly one view that is right for every issue, or are there some issues where it is a matter of personal preference?
My background tells me that there is one way for almost everything. I was raised with a fairly literal interpretation of the Bible. A lot of C(c)hurch tradition was viewed as suspect, and in some cases, used as examples for why people in other denominations were not Christians. Re-reading familiar passages while balancing how I was taught, the historical context of the text, and church history is overwhelming. I wish I was the type of person who continued to believe the way that I was raised and never had a question about anything beyond that. I never wanted to be the person with doubts. I would much prefer unquestioning, blind faith. But I have come to realize that just because I was raised to believe a certain thing does not mean that it is right and everything else is wrong. Just because some hold a viewpoint doesn't mean that it is the Christian viewpoint; it may be a denominational viewpoint.
I just wish there was a simple way to separate the two.