Interesting question, and much debated.

The "finishing the progess of insight for the first time" understanding of Stream Entry is the prevailing model here at the DhO. The thing is, to notice and diagnose the individual stages of the progress of insight, a fairly intensive meditation practice is required, and thus the focus on retreats. It is possible to do this without long intensive retreats, but the stages will tend to show up less clearly, and if one focuses on landmark experiences, which can present strongly in a retreat setting but less so in everyday life, it can be quite confusing.

There are other models - for example the Western Mystery Tradition's operation of gaining the "Knowledge and Conversation of the Holy Guardian Angel" and esoteric Buddhist/Vajrayana practices with a similar focus - which can be easier to use in everyday life, I hear, but I don't have any personal experience with them.

In the end, realizations such as Stream Entry will affect how your own experience presents - how else would they present? So by examining your current mode of experience closely and getting to know it well (for example, by doing insight meditation, or by surrendering to the actions of a deity as they present in your experience), changes in your mode of experience will also become evident when they happen. Single experiences which persist only as memories fading over time are probably not shifts in the mode of experience; on the other hand, what does happen is that after shifts in the mode of experience, the new mode will become more familiar over time. This growing familiarity is subtly different from a fading memory.

My own experience with Stream Entry is that it marked a point in time after which my mind was allocating fewer resources to upholding a facade or image for others to see (and for me to see reflected in them). This was experienced quite viscerally as a lot of harmful useless activity just falling away, with calm, clean openness in the mental space they used to occupy. Another experiential shift was that I can "incline my mind towards emptiness": I can induce a shift in perception where perception is not so intensely personal; I can look at my hands and see them as human hands, feel the touch sensations, without a heavy soft-focus overlay of "these are my hands", for example. There's an old thread called "Empty Hands" where I try to describe this and other shifts in perception.


Useful?

Cheers,
Florian

"feel-good" meditation is important, too. While there is a lot of discussion of the unpleasant stages of the progess of insight, collectively called the "dark night" or "dukkha ñanas", that doesn't mean that tranquility should not be cultivated.

Regarding whether you want enlightenment at all - well, find out! You can make a journalling exercise out of it, by asking, "what is the reason I am interested in enlightenment?" and writing down what comes up, then questioning that again, questioning the assumptions behind that answer and so on. Jed McKenna has a lot of stuff on this technique, and it has been very useful to me. There's a similar exercise suggested in MCTB (chapter "The Three Kayas")

[indent]I think that everyone on the spiritual path should occasionally sit down with a piece of paper and list their favorite half of reality that they imagine or wish would be left if they got fully enlightened, and then list all the aspects of reality that they wish or “know” would vanish forever. They should then list the things that they imagine would show up as a result of full realization that are not here now. The differences between these lists often point directly to what blocks the development of wisdom from clear acceptance and understanding of reality.[/indent]

Then, there is also the Actual Freedom discussed here. If enlightenment doesn't appeal to you, but freedom from malice and sorrow does, i.e. being happy and harmless, it might be worth investigating.

Cheers,
Florian

[edit: added the MCTB exercise]