With all due respect, you’re either deluding yourself or have not looked at current gladiator pricing. They would not be able to sell his truck new for 40k. You can buy new Sports with a msrp of 50k for around 40k.
At least near me in Tampa, the bottom has fallen out on Gladiator pricing.
I don’t have a Jeep, yet, so I really cannot comment on the ownership experience and whether or not you should keep it moving forward.
What I can comment on, however, is your buyout. Jeep does not want your Gladiator back. The cannot sell the inventory they have now. If you do decide to keep...