There's a retired army guy on the big island that rents lifted jeeps. Company is OverIsland LLC, you can find him on Turo as well. He didn't have any gladiators when I was there last (Feb 2020). But the JLU I rented was awesome!
Trade in pricing was ok. I got that ram in 05 and it had 208,000 miles on it though, so it's probably not a good representation of the trade in process. MSRP was 59k, got it to 49k before tax title and license. 52 all in based on Texas sales tax.
I just dealt with Kent last weekend. He kicked ass! I was in and out in an hour. Definitely use him though and mention this forum, the entire experience changed when I dropped Kent's name. I should have done it as soon as I contacted them.
My old Ram in the background, hopefully this Mojave...