On the quest for spiritual awakening it is not unhelpful to belong to a sangha (the spiritual "in" crowd) but it is certainly a vital thing to trust a master, or guru.*
The path to awakening is a delicate balance of despair, desire and trust, the fulcrum of which is awakened Consciousness. The awakening that took place in this life was a traumatic process that was held together primarily by the grace of the guru. And the catalyst for awakening was the trust in the guru. So there needs to be a heart connection, not a mind-juggle that convinces you that that master teaches something that you feel comfortable with. Wisdom is greater than you are, and may make you feel uncomfortable. Yet it will be healing at the same time. The true guru is the embodiment of pure wisdom, of pure Consciousness, so to sit at his/her feet (where there is no gender, no separation) is a supreme act - perhaps the final action you may perform.
Find that one who takes your heart, and leave your mind only to watch for any betrayal of your pure Heart-trust, which, (only) if the guru is truly a guru, will not occur. If there is a betrayal, then get up off your cushion and run. Otherwise stay and be challenged to the core of your being.
Trust is absolutely vital. It is the bridge that carries you across the chasm of fear. Your true nature is freedom from bondage of all kinds. Fear is most insidious - it sneaks into the heart and creates an apparent division in you. Although this divide is illusory you need the courage to cross it. It is trust that will carry you. Through your trust the grace of the guru manifests. Trust is the intuited knowingness (instead of mental knowledge) that your guru is on the other side, beckoning to you to come across in safety.
I have been blessed twice in this life (and more) to meet masters with whom there was an instant connection. Actually it was overnight before I woke up to the realisation that Shantimayi was the guru that I had been expecting (and that's a whole story in itself); but with Bhim Giri Ji, in India some years later, it was immediate and unexpected. I simply belonged. It was amazing to sit in the presence of a naked man covered with ash as if it is the most natural thing in the world. (Perhaps it is!) Bhim Giri was not contained in his body. I was actually sitting in him. It is the only time in this life to have been totally and tangibly embraced in love. Words are inadequate.
The connection between guru and disciple is not normally chosen by you. The little finite mind cannot wrap itself around the infinite cause. Rather it is the universe conspiring for your awakening that causes such connection. And when you are open and ready, the guru is there. It may take some time before he is revealed, but time is not relevant in this quest for immortality 
As Thoreau said: "Any prospect of awakening or coming to life to a dead man makes indifferent all times and places. The place where that may occur is always the same, and indescribably pleasant to all our senses."
(* Since all is grace, "vital" here does not mean "necessity".)
Janak, thank you for this post, there are a lot of words here that relate to my place in the realization of true awareness. It's odd, I don't feel I am seeking, but that it is looming in front of me and will overtake me. Finding/accepting an adequate teacher right now seems important. This is a helpful guide for that.
Never forget that what you seek is everywhere, in the master, even in yourself.