I always buy late model used with low miles.
My current Tahoe is an '04 that I bought in '10. I just kind of happened into it not really looking at the time. I was driving an '01 Tahoe with 180k on it and I had actually stopped in to look at a 4 door Nissan Frontier with a 6 speed. I saw the Tahoe in the back and it was sharp. Fully loaded and only 33k miles on it. I made them an offer and they laughed. I told them to call me when they were willing to make the deal. The called a couple of times to make counteroffers, etc. but I stuck with my number. Finally after a week they called me back and told me to come do the paperwork. I paid roughly 1/3 of the original retail price for a vehicle that looked like it just rolled off the showroom floor and only had 33k miles on it.
Those are the types of vehicles I buy. I'm never really "in the market" for a vehicle. Once I'm over 150k, I just start keeping an eye out, go ahead and get preapproved through a credit union for a low rate, and then when I find the right deal I jump on it.
"People say that marijuana smoking is going to get in the way of my career. I say to them that on the contrary, my fighting career is getting in the way of my marijuana smoking." -Nick Diaz