Originally Posted by TackyTiger
I suffer from insomnia and listen to audio books on a rockboxed device with persistent sleep timer set on (Sansa e200v2, very similar internally), through a passive speaker. I find the volume through the unamplified speaker easily audible at half volume, and there's nothing to roll over and crush that way.
I like to do over the ear headphones for my method, though, as it cancels all other sounds in the room (we have multiple dogs). Once I start to feel myself crashing, I simply take them off and go to sleep. I repeat this in the middle of the day since I can't sleep for longer than 2 hours at a time.