For your first post, I think that the best timing and also the method DEILDing is only something you can find yourself. Look at your successful attempts and compare what you did then to what you do now. I am sure you can find something is different, not only what you did but also how you did it, for example bedtimes, amount of stress in your life, and even your own question, just look at how many alarms you used then and know that you can be successful with that, but feel free to experiment of course.
For your second question of why you had regular DILDs from time to time but that stopped now, but you struggle a bit with it now.
My theory is that you as a younger child just was interested in dreams but wasn't so concerned about the result as you are now.
I had the same problem, less than a year ago actually, and what I did was to do the methods I thought was entertaining to do (I use meditation and I like to meditate myself to sleep). But the point here is that I perform a lucid dreaming method or induction because it is fun and not primarily in order to lucid dream.
Use the method don't let the method use you. And remember that what's most important for succes with lucid dreaming is not what you do, but what you think.
Another good approach is to let go of the idea of the goal of lucidity completely and replace it with the goal to learn about the practise of lucid dreaming as a science or atleast a quest for knowledge.
That way you can observe instead of judging the attempt and you can find joy in learning from the attempts by appreciating the unsuccessful attempts as well.
Don't hope or try, instead learn and observe and this will in a calm matter take you torwards mastery and understanding.

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