So, retard here with my opinion:
I've had 3 Gen 1s, one was supercharged.
I have 1 Gen 2, recently bought.
For the same budget, I would go Gen 2.
My last Gen 1 was a 14 RR that had 41k miles that I bought for $41k. Now, the same truck would cost more.
Great truck, but man even with it being a FL truck it had rust, and in hidden areas too. I still love the look of the Gen 1, and knock on wood they are reliable but to me, if you want to offroad the truck, the Gen 2 is a better platform to start with, due to it's weight and improvements in suspension/frame due to things Ford has learned.
If you can find a clean "factory" roush Raptor or shelby Gen 1, then that to me would be a tougher decision.