Thank you for sharing your deep thoughts on this matter. Yours is a very complex question, and therefore I won't try to answer all of it at once. However, here are some preliminary thoughts.
First of all, be assured that transformative experiences are not that easy in their possible repercussions. I get many letters from people who have somehow triggered Kundalini before they were really ready. The result can be anything from general discomfort to intense pain, including physical and mental suffering. Some fall into heavy bliss states, only to find that these states do not last for them and then their sense of loss is intense.
Therefore, the advice I give to anyone longing for intense transcendence is to prepare and purify in every way possible. First and foremost is to clear any psychological issues that are still unresolved. Kundalini tends to act like certain drugs--it makes you much more aware of everything that is hiding under the surface. You may virtually relive past traumas, and awaken latent physical illnesses. If you are having difficulty dealing with these issues now, be assured they will now become many times over more alive in your awareness. And--even if the immediate effect of Kundalini is bliss, you will be required at some point to go back and face whatever is still waiting for resolution.
So--my advice is always--get your personal psyche in order as best you can. You need to be as strong and integrated on all levels as much a possible to take this journey. Of course, no one is totally prepared--we all have unfinished business, but sometimes the event chooses its own moment and then we simply have to deal with whatever reality we find ourselves in.
And it may take a very long time. It took me over fifteen years to reach a point of mental/psychological stasis--and even now I can get "thrown off" in surprising ways.
In truth, I paid a heavy price for whatever progress I have made. I don't know why I (of all people) have had the experiences I have had. Indeed, I have known more than my share of "bliss." But for many years each moment of bliss was accompanied with an equivalent measure of pain.
I think it is good to ask for what we desire--but I also think we should remember to ask that the wish be granted only "when we are ready."
None of us knows what exactly is our proper "place" in the spiritual hierarchy. I think we should ask to be granted that which is appropriate at this juncture in this lifetime. We are constantly progressing, transforming, changing into something other. It is that journey, that constant opening to and acceptance of what is granted that is important. We cannot "make" it happen, but we can "allow" it to happen, at the right time.