I also used to be a bit of an insomniac, and one sleepless night could easily throw off my circadian rhythm, creating all sorts of extra anxiety, which translates into demand avoidance, stress and furthering depression.
I had a stint of a few years off of medication to see how it went, thinking that I was sufficiently practiced at introspection to know if I needed to start again.
I was very wrong, and put it off far too long. I've been back on medication for about 7 years and don't plan on stopping, ever.
Wellbutrin and effexor both worked alright, but I felt like I needed to keep ramping the dose. It is also possible that I was poorly managing my stress in high school and college. Ultimately I topped out at the highest dose, and ended up getting anxiety issues (never medicated) on top.
I don't recall what I switched to after, but that was the point I tapered off of meds entirely for a few years.
I ended up back on Lexapro and it has been a life saver. I also started up therapy with the Lexapro, which I realize in retrospect I should have been doing to much sooner. After a few months my therapist said I didn't need regular sessions any more, and I haven't been back since.
That said, I'm aware enough to know it is a bit of a balancing act. Managing my stress levels is the biggest thing, and if something significant and negative in my life were to happen, I'd probably start up again.