When do I know it's time to try?

EDIT: Thank you all for the advice.

If you ever have time for an afternoon nap, that's the best time for WILDing, in my experience. You're not too tired, and you have had some experiences during the day that may help you dream, and you are also very likely to go straight into REM at that time.

I try for WILD and DILD at the same time, every time I sleep, 4 or 5 times a night, but I would not recommend trying anything unless you know how long it could take to work and exactly how to do it so that it doesn't stress you out trying to follow something on the nose when it is just supposed to be a guide, not a step by step walkthrough. Always lean to DILD, because if you concentrate too much on WILD it can cause insomnia.

5 days is a very very short time to do any hobby, remember, don't think of it as something that you are gonna do now for a month and then be able to the rest of your life. Think about it as a hobby.