You've got to give us a little bit of a chance here - this is a discussion board, not a live chat.
Anyway, I'm no expert, but I do have a couple thoughts:
First off, the bent/kinked cooler lines - where between the rad and the trans did you see this damage? If it's against the engine block above the axle, this is a common spot for a bit of "crimping" to occur if you run with the front swaybar off and flex the truck out, because the passenger side upper control arm mount swings right into that spot if the bumpstops aren't set right, particularly if you're lifted. Depending on the history/usage of your Jeep, this might be expected. How badly kinked are they? Mine have had a bit of a crimp for years, and don't seem to have caused any issues for me.
Moving on, the "returned" leak. I can't speak to the gouges you saw in that ring behind the seal (but in general, my understanding is that any "damage" to a sealing surface is a bad thing), but I would like to ask how much fluid you put back into the trans after doing the seal, and where it showed on the dipstick after you noticed the leak had "restarted".
I ask because of something that happened to me back in June - I was coming to the end of a 2 hour drive, and purely at random I noticed a cloud of white smoke pouring off the back of the truck, so I pulled into a Tractor Supply lot I happened to be right by (I'd just come off about 80 miles of interstate highway cruising, followed by a long climb up and over a mountain, and while the temp gauge rose a hair above the 210 mark, it didn't go more than a needle's width and came right back down once I crested the peak and started down the other side). I climbed out (leaving it idling), and looked under the truck and saw ATF dribbling out from the bottom of the bellhousing.
Thinking I'd just blown the front trans seal (and being worried about possibly having to call AAA to get towed 100 miles back home), I immediately popped the hood and checked the trans dipstick, and found it reading _above_ the "hot full" mark. I went inside, bought a 2-gal jug of ATF (wasn't sure how much I had onboard in the back), and set out for the campground where NACFest was headquartered. Got up to about 50, and got another white cloud out the back, which really unnerved me, so I backed off the throttle and eased/limped it the last 3-5 miles. Checking again at the campground, the level still showed above full.
Next morning, same thing - still above full, so I headed for the trailhead. No white clouds on the way there, which included a substantial hill climb at the end, and when I checked in the parking lot there, I was down to full. One of the guys I was meeting there, when I related what happened, said he's seen that before with the AW-4: if overfilled, that front seal can just "burp out" excess fluid and seal right back up, and that seems to have been what happened to me - I'd replaced the trans pan 5 or 6 years back and apparently overfilled it at the time due to inexperience, and it just picked last June to finally blow off the overfill. My fluid level's not moved since, and no discernable change in trans behavior either.
TL/DR: Overfilling the AW4 can sometimes cause it to "burp" excess fluid out around the front seal without actually damaging it.
Just something to consider...
