3 months on BCP or Vitex, which is better for pink?

I have been pretty set on the Vitex, but since I took a break from it for 2.5 months, it may delay O again the first month or two. Plus, while when not taking anything, my cycles are usually 28 days, they can and do vary and I've had a few longer cycles (31-35 days, plus one 41 day one my first month on Vitex) since I began swaying, I think at least partially due to dietary changes (especially going from 60% fat to 20-30%). Right now, if my next 3 cycles are close to 28-30 days, and I keep Oing around CD18, I will O around Dec 4th. The timing is important bc I am aiming for a due date as close to Sep 1st as possible, and I'd like to keep any potential late due dates around the 1st of the month if I don't conceive my first cycle trying. (Yes, I know all this planning is uber-boy-mommish, but I'm set on this. I'm trying to get the planning out of my system in advwnce of TTC.)

If I take BCPs for 3 months, the timing will be perfect, and in the past I have always Oed in a timely manner coming off them. Probably bc I usually O on the pill anyway, or did 10 years ago. The pill dries me out much more thoroughly than Vitex & diet, so there is that, too. And I could maybe get clomid (I'd try 25mg, and I'd try to get monitored) to further assure the timing. Or maybe I could take Vitex while on the pill? I'm afraid if I started Vitex right after stopping the pill, it might delay O.

Or maybe I should TTC while ON the pill, if I can confirm I still O on it and do for those 3 months? Ladies, what would you do if you were crazy like me?

I know I'm totally overthinking this, but I also know I will skip a month if the timing isn't right (I have already) and since I want Sep 1st, Oct 1st, Dec 1st, or April 1st approximate due dates only, I don't have many chances in the year as is. And of course, trying to sway pink my hardest would be nice, too.

I wouldn't bother trying to TTC on the pill, it will be a waste of your timing.

In the past I have, that's why I considered it as an option. I would definitely only try one month, if I didn't conceive right away I'd go off the pill.

But now I'm thinking Vitex + pill would be best for my 3 months, then go off the pill but stay on Vitex for my attempt month. If it is safe to take them together?

WE don't have the data to say for sure but my gut instinct is that BCP sway harder than vitex.

would not TTC while taking pill as odds of conception/successful pregnancy are low

Alright then, the pill it is. It will be less stressful for me, too, to know the timing will work out. I'll have a bit more leeway if I O late coming off the pill. Thank you!