Scarlet, I'm glad that you're happy with getting off the pill. I did it about a year ago...and I love it!
For your first question, when to start taking Vitex, DQ, I don't know the specific answer, but I started about day 10 (just a chance start). I think many people, especially those with super long cycles/no cycles, start in the middle of their cycle. If you've just finished with the pill, and are starting your cycle, now would be a great time to start taking the vitex/dq.
The only important part to remember with DQ is not to take it during AF as it will make you bleed more.
When you took vitex before, did you take it your entire cycle/only pre-O/not during af? I only ask out of curiosity as usage patters vary. Personally, right now I take it my entire cycle (I've been on it for about six months), although, when I start ttc, I'll probably only take it pre-O (unless I start to lose its effect...which won't happen since I'll be pg soon

).
Congrats on the diet changes...I really think my improved nutritional status has made a huge difference in my health.