Ok, this is the first idea that meshes with my limited appraisal of the leak. I am going to have to look at a schematic to get a better handle on your suggestion. I like it. Thank you for taking the time.Whether you remove the rack or not is a personal decision; I can't offer any useful opinions there. Your A pillar leak is the sunroof. The front drain hose is not draining causing the pan to fill up and run down the A pillar.
Pulling the drain plugs in the rocker panel, cleaning the drain tubing and pinch welds will not solve this problem. All that may help, but the problem is in the drain design.
The permanent solution is to run the drain hose through the floor. You can either a) use the floor hole Toyota provided under the floor mat (not my choice), or b) remove one of the body panel screws securing the rear edge of the fender to the body and drill out the weldnut in the floor of the well to allow you to run the hose through it.
You can either a) use a smaller/larger diameter hose to extend the hose, which doesn't currently reach the floor of the well the harness is tucked into, and into which the sunroof drains, or b) swap the front drain with a rear drain. Same size, extra 12" longer; it'll get through the floor of the well and extend about the same amount as the current rear drains do in the rear fenders.
Funny, this thing spent the first 24 years of its life in Old Town Alexandria