Thank you to everyone who has posted and messaged.
Key fixes:
1) exchange 1000 pound spring bars for 1500 pound bars
2) Raise the ball 3 inches
I just spent 90 minutes with my neighbour, who has the same Blue Ox Sway Pro system, same truck, and almost the same trailer (his is 2 feet longer).
First words out of his mouth "your trailer ball is way too low!"
He drove home and brought back his hitch head assembly. His ball is a lot higher than mine is.
I asked him to bring his spring bars too. They have 4 dots so they are 1500 pound bars compared to mine, which are 1000 pounds.
We use Jason's hitch head assembly and he proceeds to hook up the bar on the passenger side. They go on surprisingly easy. I mean completely different than what I have been struggling with. I do the other side and can't believe how simple this works. We didn't have to raise the trailer and truck that much either.
We drive the rig around the block and park in a flat driveway just up the road from me in front of a private garage. Lots of room.
Time to unhook, level the trailer, and take some measurements. I install my hitch head assembly.
22 3/8 inches to bottom of coupler
19 5/8 inches to the top of my ball
That's 3 inches too low!
I measured to the bottom of the fenders on the driver's side wheels before hooking up and after (while using Jason's Hitch Head Assembly). The truck goes less than a couple inches down and with the trailer leveled by using the correct chain link the rear of the truck sits a bit higher than the front. Perfect.
So that's it folks. Wrong bars and trailer ball is too low.
During all of our fiddling, hooking and unhooking, with his hitch head assembly and 1500 pound bars there were no issues, no scary moments, and no fear of hurting yourself.
So time to make a few changes and tow happily ever after. :-)
