O.K., lets try to piece this together.
Authenticity and breaking taboos....
I don't break taboos, I ignore them. As long as I'm not hurting someone else, I do what feels right to me, regardless of social "norms" or expectations.
I make a Time-Line chart that shows one creative way I would break with convention (authenticity). Graffic Arts, collecting and disiminating information.... my way. (that t-square?) I am very artistic, but I see myself as more of a scribe (good hand-eye coordination) than some kind of creative genius. (Lilith in Cap square Mercury-Mars?). Art nurtures my soul, it's a form of meditation for me.
I can't play games. If I get caught up in games, I loose. It's as simple as that. The most obvious experiences of that is in the workplace, where games are sometimes the path to success. I deal with it by working twice as hard in order to get recognition for doing a good job. I actually like that about me. I don't consider it a problem, but have to accept the idea that it doesn't always turn out well. When the games start, I Loose.
I also hear Lilith describes the men your attracted to. My Lilith is ruled by Saturn and, boy, have my relationships been described by my Saturn. Saturn is also connected to Lilith's t-square, by a trine from the 12th.
As for the transit, Scorpio is intersepted in my 4th. My mother was a Scorpio, she worked with the law (Jupiter in Scorpio) which shaped my values (Jupiter trine Venus, loosely trine Saturn). She had 4 children, and out of all of us I'm the only one who carried forward with her hardest life lessons. (Pluto conjunct the ascendant? Moon conjunct the Sun/Midheaven?)
I feel like Scorpio is a huge vortex in my chart, drawing me in to the void of a reality that has nothing to do with this world. It seems to be my life's mission to blast that reality into the known world.. but after 63 years it's still very much a work in progress. (or is it a fruitless effort?)
Pluto itself is very strong in my chart. I work well with him. He doesn't scare me, anymore, but he does frustrate me. I want more from him and I want it faster.
Because of the close orbs, I consider this transit as triggering the entire t-square, from almost 6 degrees to almost 10 degrees. I'll get a hint of it this spring, and will deal with it all of 2012 and most of 2013. Uranus will also be involved most of that time, transiting my Mercury-Mars. Lilith, being the apex of the t-square is a blank space I'd like to fill in.