Does one, at some point in their life, make a moral or ethical conscious choice to become enlightened or to have enlightenment experiences?
Is it experience, mystical or otherwise, that either leads one to the path of enlightenment or to automatically 'become' enlightened? Or does one become familiar with the term and its definition and make the choice to seek enlightenment?
What measure of discipline, if any, in your opinion, does it take to become enlightened or to have an enlightenment experience?
Most importantly, is my fashion sense really all that bad?
To Question 1: I don't think so. Enlightenment in the Buddhist understanding transcends the self and other paradigm of all choice.
2) The Buddha is someone that had experience to talk about that, while I have only speculations. One that does stick out to me in the discipline department that he spoke of regards sex. The Buddha chastens one of the monks very seriously in the monastic rules because he allowed himself to be coaxed into sex by his family and former lover.
The Buddha said in very strong terms: I have told you that one tied down by such things cannot even achieve a jhana, much less Nirvana
3) I mixed up questions 2 and 3 it seems. I am tired, so consider this question 2's response.
In Buddhism one can touch enlightenment spontaneously, but there is an element of ignorance. It's like a kid playing with a fire without knowing what they're doing. Knowledge is one of the necessary aspects to perfect enlightenment. That's why no Dharmic religion encourages solitary practice without a teacher.
A person that randomly and briefly touches Nirvana has no idea what to do with the insight gained, especially if they are still bound in all kinds of appetites.
4) I don't know what you'd expect me to judge your fashion sense by