Welcome to PY, on my old '69, I worked for quite a while to get the bumper and taillights to line up. What I found was that the taillight stud holes drilled in the rear tail panel at the factory were far from level. Put a level on them and the bumper and see which one is off. I ended up removing the taillights and taking a porting burr and oblonging the tail panel stud holes to allow the taillights to be aligned properly and level. It came out fine once I worked with it for a good half day. Since then, I have noticed most every other '69 GTO I saw had the same problem. I'm not saying this is for sure your cars problem, it could be the bumper, but check the taillights alignment for sure.
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