re: What year model would be your cutoff for a 4-Runner?

I don't like the look of the 4th Generation models (2003-2009 model years) nearly as much as the 3rd Generation or 5th Generation.

Sales showed that as well, they went from selling 100K+ per year down to 19K in 2009... then back all the way to over 100K units sold in 2016.

So, with that said, if I was you I'd scratch option 2 first, and either go cash on a 3rd Generation 4Runner, or suck it up and finance a newer version. Really depends on how long you want to wait until you buy another one.