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Most of the imagery on the tape pops up later in the film... like the blood in the water coming from the horses, finger on the nail happening in the well, etc. A few things weren't explained... I would bet they were just supposed to be creepy.
"You weren't supposed to help her" referred to Samara's manipulation of Rachel. She managed to get Rachel to feel sorry for her so that Rachel would remove Samara from the well. That apparently helped her (to become a more effective ghost? I don't know). After the scene where the kid says "you weren't supposed to help her" there's a montage where Rachel sees/hears stuff with Samara again in a different context and begins to understand that she's a Bad Ghost and was better off in the well.
Part of the reason that the film is hard to follow is that it is a remake... they changed a lot and expected it to still make sense.
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