I haven't been doing this long, but I have a story that applies. My last trip out to Savage Gulf, I brought along my first DIY hammock. It was made of cotton based rip stop, which I know isn't ideal, but it's what I could find locally in time to go that I felt good about given my weight (280 at the time).
Now, originally, I was planning on sleeping in the tent for what was to hopefully be my last time as I was working towards converting to the hammock as my shelter. It wasn't too cold (41° low), and I was unusually uncomfortable on the ground, so I decided that I was just going to get back up, and try sleeping in the hammock tonight.
So I took the sleeping bag (20° synthetic) my pad, and fleece liner with me into the hammock. Now, I hadn't made my tarp yet. Everything was going great, until I felt some raindrops on my face. I proceed get rained on for about 1 minute. I sat up right before I was about to throw in the towel and retreat to the tent, the rain stopped.
It was just enough to make me uncomfortable, and I was waking up constantly checking the sky and wondering if I was going to get rained on again. Once I saw a clear sky and stars, I was able to get comfortable again and sleep like a rock.