F250 would be my first choice, gasser not a diesel. Used, under 50k on the mileage.
You're on the mark with where I'd be kicking around in my parallel search for a Tundra
Plenty of them F250s for sale. Good luck on the decision Jesse, lots to digest.
I think you summed it up well with one word "safety". I don't want our trips to be a white-knuckled, butthole puckering event either. I knew when we agreed to buy it, I'd either need to sink $ in the Tundra to upgrade it's towing capability, or bite the bullet at jump up to a 3/4 ton. I think I'd rather have the peace of mind and deal with a slightly larger vehicle. MPG can't be worse than my 5.0L at 13.5 can it?!?