St. Simeon the Stylite is very inspiring as someone raised Anglican. But he was moved to preach to droves at a certain point, to be a salt of the Earth, to be surrounded by others.
My interest is mainly on an historical level. You're right about St. Simeon eventually preaching to multitudes. But the original intent of those early Christian hermits was to go into solitude to contemplate God. The English word 'monk' derives from the Greek 'monos' meaning alone. It was only later that monks formed large communities. Even now there are monks who say their only work for the world at large is to pray for it. But I think that kind of life could only ever appeal to a very few people.
I'm probably the prototypical Christian loner. I'm not affiliated with a church, but take fellowship regularly with three other groups of Progressive Christian loners. The Churches that I do attend from time to time, are mainline Protestant churches--Methodist, Presbyterian, Disciples of Christ, UCC, and Episcopalian-- which are really open minded on matters of scripture and doctrine. I like the people and the message and think they're dong real good in the world. But the tradeoff between togetherness and conformity often leads me to opt out on Sundays. I guess I share all the feelings the good preacher in the video mentioned that were responsible for his loner status in his youth. Ritual and hymn singing does nothing for me, and I don't find the canned spirituality of the churches satisfying. Contrary to the preacher, it's the institutional Christianity that often strike me as fake. One of the problems is that I think orthodox Christian doctrine is flawed. Paul took us off the rails in the first century by emphasizing the death and resurrection of Jesus instead of His message and example. A succession of church fathers from Irenaeus and Athansius to Saint Augustine compounded the problem by coming up with creeds and doctrines that I think are wrong or irrelevant. So at the part of the service when we say the Apostle's Creed and the Nicene creed and profess our belief in unbelievable things I have to bite my tongue and remain silent. No big deal. I know many of the others don't literally believe them either and are able to live with metaphorical interpretations. In fact we've discussed this in my groups. I realize that others draw much support and strength from the Church community, and if I want to advance the work of the church as an instrument of organized altruism, those are things I can put up with. It of some comfort to know that a leading Oklahoma pastor, Robin Meyer, shares some of the same thinking as mine in Saving Jesus from the Church: How to Stop Worshiping Christ and Start Following Jesus.