Starting repair process will document best I can.
Started by reviewing this video on replacing the seals:
While this gentleman was very nice, he neglected to point out to n00bs such as myself that there can be locktite in the door stopping thingy threads. I noticed but forgot to clean it out before replacing. While I got lucky on the right side, mangling of bolts and threads ensued on the left. Documented here:
I bunged the door threads on my poor old Gen 5 (2003)

have to remove the door stop thing to replace outer door gaskets. The video I watched failed to remind me to clean off the locktite. Doh!
Got away with it on the right side, but not the left. So begins my first adventure with a tap and die kit. Kits abound at Home Depot etc, but no cutting oil? Had to borrow from a friend. Fortunately Home Depot had the 8mm, 1.25 pitch flange bolts I needed. Then the next challenge, you'll notice the tight space on the left rear area, the kit didn't come with an extension. After watching a video on using a power drill for tapping that made me nervous, I remembered: I am a pack rat and I can do this old school
What a perfect match, for a 280K car. Success!
But the front left has even less space. This pack rat doesn't give up so easily
Unfortunately, I wasn't able to get the "leverage" I needed to tap the even more bunged up thread there. So I had to add to the tool collection.
I got lucky and Amazon could ship tap extensions the same day on Prime. And I am back to exiting my car without fear!
I ordered the outer gaskets from OEMpartsquick.com, couldn't find them on Rock Auto, which I thought was strange. That company was fine, they showed up in a reasonable amount of time, but the gaskets were mislabeled both in the bags and the invoice. So I had to offer them up to make sure I had the right parts after the bag I opened was NOT for the left rear door. I was able to figure them out matching each.. starting corner, for lack of a better word. I matched them up inside the bag in case a return was in my future. It all worked out but it was an unwelcome bit of stress.
I am glad that i did this while the weather was warm, much easier to work with the plasticky bits. Especially the plastic keeper pieces on each rear door. I broke each one at the top, so I need to remember to order replacements when I get to the inner seals. I would probably have completely broken them both in the winter time.
These were Toyota OEM, and in line with Toyota's reputation for high quality. The plastic anchors were color coded for matching up mounting points. I was amazed how easily they aligned themselves back in their homes. A truly clever bit of engineering in my opinion. Other than the left side bolts, the whole process was very easy. For any others that do this, please make sure you clean that locktite out before running those bolts back in!
Looking back, I think I didn't fully review the video before ordering the parts. Had I watched the whole video, I would have known to order inner seals as well. While I want to order replacement rear door "keeper" things for the outer seals... I don't know I'll be holding on to the car that long. I've put so much money into it this year... I just don't want the thing to rot out on me.
Started by digging out the rot, then will dremel sand. Here's an odd thing: the wind roar has gone away, I'm almost certain of it. Would hear it before as low as 30 mph. Had it up to 60 and I think it's gone!
EDIT: Wind roar has nothing to do with the outer door gaskets. It came back when I opened the window. Once I opened it by accident at highway speed, and the noise was TERRIBLE after that. Eventually it "resettles" and quiets down. So it seems to be something with the seals inside the window track, by my estimate.