Figured I'd just keep updating my own topic in case it comes up in the results from Google or someone in a similar situation. I feel like I finally "figured out" what the problem was.
I ended up buying both rear drain hoses.
Part # for those who might need them:
4M0-877-203A left rear
4M0-877-204-A right rear
Tackled the replacement today, no different than me trying to fix the issue before except in addition to removing panels I removed the wheels from their respective sides for installation of the drain hoses. I did find it much easier to feed the hose through the wheel well inside car for the grommet to lock into place. Rather than the other way around.
Once I moved some foam and carpeting pieces out of the way on the passenger side, it was quite apparent what the issue might potentially be. It seems like the hose was kinked, I guess overtime there was enough build up or whatever that it just leaked. It only leaked inside on the major downpours, which throughout the life of the car, there really hasn't been all that many it's been through that I know of.
Drivers side didn't have that issue.
Hopefully this is now fixed..
Did not add any extra silicone or anything this time around either




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