I have a shower that is leaking into the neighboring drywall. I believe it is the curved door track that is the culprit. I have stripped away the old caulking, and I'm preparing to re-caulk. I stripped away caulk that was in the track and at the base of the wall jamb. I have read about weep holes, and am not sure if I should re-caulk everywhere where there previously was caulk. Based on the images linked to below, can anyone advise me as to whether I have a weep hole, or whether or should be caulking the whole area?

I'm a little surprised to see the gap between the track and the wall jamb. Does that look correct, or is the whole thing not installed properly?

Thanks in advance!