Have you ever bought the dip, but then the price breaks through the support and continues dropping deeper for weeks or months?

Well, I have done it before.
I don't think people can easily catch the "absolute" dip, but if someone does manage to buy at the most perfect time, I assume it's just pure luck. And I'm speculating that almost everyone here has been in a situation where they bought the dip only to discover that there is another wave of distribution coming.
The best way to take advantage of this opportunity, in my opinion, is to place multiple buying orders at different price ranges that you believe are support/supply zone candidates. This also implies that the size of your purchase order is determined by the probability and accuracy of your T.A.