
I feel for you, I really do. Because I obsess about things too! Especially breeding things. I've got a birth coming up in a few days, Nimue's first ever, and already those what-if thoughts are becoming ever more present in my mind.
Here's the shake you asked for:
Just go for it now. Stick to your plans, trust the male, trust yourself, it will very probably work just fine. If it shouldn't, the timing was likely not the reason. I can tell you, I don't know very much about all these tests you are doing, but they would drive me completely crazy. I did one progesterone test once (not wanting to inconvenience the stud-owner unnecessarily), and it sent me running to the male on day 8. The male yawned and went to sleep in a corner. He mated her on day 14. She had 3 pups. With my (small) dogs, day 14 has always been the "magic day", meaning the first day the the mating worked (as opposed to the days before, when, despite all efforts, they didn't tie or the male wasn't really all that interested or whatever). My experience has been that matings between days 11 and 17 usually produce the desired results. And don't forget that everything about breeding always turns out in some way different than what we had expected, imagined, assumed, feared, read about, etc. Everything! Is this your first litter? I wish I knew what breed you have, but I know we are not allowed to say. I have absolutely no idea if your are breeding chihuahuas or mastiffs.
I think mating on day 12 is a good bet, and if the male shouldn't yet be interested, you just stay a little longer and go for days 13 to 15. I'll be thinking of you, and asking you to "hold your thumbs" for Nimue and me next week! I've got to go put up the "Wurfkiste" (the big box especially for newborns and their mother - made in England!) and have everything all spick and span before the big day arrives (gulp).