Ha! Some of it is obsessive - no doubt. I appreciate your input.
My first car was a 4-door 510. Being just 16, it was a prized possession, and I used to wash it about every week. Water got into that car and under the floor mats something fierce. One day, to trace the sources of the leaks, I set up a hose so that water showered down heavily on the car. After about 20 minutes, I got inside and looked to see how water was getting in (I had removed the kick panels and floor mats, etc.). I was quite surprised to see that a main point of ingress was one of the bolts clamping the LF door hinge to the car. A steady stream of water was wicking along the bolt threads from outside to inside the car and running downward from there, collecting into a pool on the floor. Interestingly, though I thought the windshield seal might be leaking, it was not. I also recall finding that if I pointed a spray of water from the hose at the c-pillar vents, water would fly in... it would get directed upwards by the internal part of the vent, and then drop down onto the trunk floor, where gravity would direct it to the lowest area under the rear seat bottom.
When I restored my first 240z in 1993, I had to reconstruct the dog leg areas of the car with new metal. A few weeks after I got the car painted I was shocked, and upset to find standing water in the dog legs of that car. I couldn't figure out how it was getting in and just drilled a hole in the bottom of the dog leg area so the water that was collecting there would drain out.
For this car, I'd like to know that when I wash it, or if I get caught in a thunderstorm with it, no water will enter through the emblem holes and dribble down into the dog legs, or down into the back edge of the rear hatch. Newer cars tend to utilize water proof solutions like this BMW clip, which utilizes a rubber plug, of sorts:
Given my previous experiences, I figure I might as well address these known water entry points.