I would also say that if you have not yet attended any services, the thing that ought to be highest on your list is to get to Church. You need to experience the liturgy, and find yourself in the community. Hopefully the Church there has a good community to be involved with. Every one I've seen has had, though I've heard a few people say that some Churches do lack that.
But Orthodoxy isn't something you primarily get through theology, or ideas, or history, etc. It's certainly a great starting point - it is how I came to become interested. But I'd extend Katherine's analogy (which is a good one) to say that being an inquirer who has not yet been to Church is more like browsing ads for mail-order brides - a far cry even from dating.
The distance - I understand you want it to be closer. But for the US, you have no idea how blessed you are to have many parishes within 10 miles! I travel almost an hour on the interstate to get to Church however many times I go in a week, and for the part of the country I am in, I'm even fortunate. Another lady I know in Florida must travel about 2-1/2 hours, so she has to go stay overnight with someone just to go to Church on a Sunday. If someone 10 miles from the Church needed a ride on my way, I'd be MORE than happy to stop and pick them up. I'd be equally pleased if someone out my way wanted to share a ride. I also doubt a mission parish would be a high priority in such a situation. Remember, there are quite a few Churches out there that do not even have priests, and need to wait for one to come serve a Divine Liturgy once a month or even less often, and can only have reader services otherwise. And people drive long distances to get to them as well. They need priests more urgently.
Family can be difficult, and the Orthodox Church is so different from Evangelical Protestantism, especially mega-churches and especially if they happen to be the "relevant" sort that deliver entertaining and focused services that are crafted to serve the interests of the people and get them in and out in an hour or so. My brother and sister recently started attending church, and it is one of those churches, so I don't even bring the Orthodox Church up to them right now. I've been a family outcast as far as religion is concerned much of my life, and this would be no different.
It's good that your friends would likely be more accepting, and especially if they have similar interests and would be likely to have productive dialogue with you.
As far as coming across to others - a "soft sell" is much better. I would suggest you to wait. Attend Church. Start doing a prayer rule. It will almost surely start to change you, and they will probably notice, and when they ask - that is a good time to start giving soft answers. They will be interested, and you won't have to push. The difficult part is NOT bubbling over with enthusiasm and having all kinds of discussions in the meantime - at least that was the hard part for me. And for people who oppose your choice, that is not what you want to do.
Just very briefly speaking, I don't have too many experiences with too many different parishes in many jurisdictions. However, I will say that my home parish (Greek) is more formal, more ritualistic, etc. and my husband who is very opposed to Catholicism did not react well. However, he also attended a little OCA parish with me that was in a temporary building. It was less ritualistic in the most visible ways (with the exception of the way the bowing is done when venerating icons) and he was able to better enjoy it. He also prefers the singing mode to the formal chants at my home parish. It might be worth considering what your family is likely to accept/reject, and see what parish is more likely to be less shocking or jarring to them if you ask them to visit with you.
I don't have any suggestions for approaching people at your church. It is so different, that would be difficult. But studying Church history seems to be a good way to open people's eyes to the fact that "things are not as we have always been told" (from an evangelical perspective). Just a slow introduction to something like that might be the best bet. But if church leadership saw it leading in a different direction, they would be likely to squash that quickly. And I don't mean that to speak badly of them. If they think what they are doing is right, it is their responsibility to protect their flock. Such learning and changing of mind and way of thinking can take a long time. I honestly think some people just are not ready for it, which is why I don't discuss it with my brother and sister yet. May the Lord please forgive me if I am wrong in this. (Just my opinion on this stuff.)
God bless you.