I guess for us the biggest factor is that it wasn't going to be an everyday driver for either myself or my wife. We both drive cars.
If it were going to be an everyday driver, and I had the money, I would more than likely go with a new truck.
But for us, it's not even close to being one....so there was no way.
But as was mentioned, with any used, and older truck, how it was used and taken care of is very important.
We searched for months before buying our 2000 F350 back in 2011. I drove to Wisconsin from NW Ohio to get it. We were VERY specific about what we wanted (crew cab, 4 x 4, longbed) and the type of shape it was in. Our diesel only had 109,000 miles on it, and was exceptionally clean inside and in good shape on the outside. It had obviously been well taken care of. We got it for $16,500 cash from the dealer and have been very happy with it in the 3 years we've had it.
You just have to do your due diligence, especially when going with a used vehicle.