Update. Towed the boat back to storage and ran it manually. If left alone wants to jump between 4th and 5th. Bumping up to 6th and even 7th on the flatter areas helped tremendously and ended up driving most of the way in 6th. For me 6th gear seemed to do the best, able to handle the small...
Pulled my boat with the Gladiator and did okay. Mostly flat roads and could tell the boat was there. Might try manual mode next time to adjust the gear as seemed to run around 3500 - 4000 rpms on small hills. Stayed around 65 and 2500 rpms on flat ground. Boat and trailer are around 5700lbs...
Joined the JT club from the JKU club. Picked it up last week and has been smiles since. Lots of people looking and stopping to ask about it. Kept wheels and tires from JKU and swapped them.