I had originally hoped to buy a 5-6 year old Tacoma with 50-60K miles, but those trucks all still seem to be $35-$40K with a crew cab, 4WD, low to mid trim options, and clean title.
I also thought I make pretty good money, but with the housing market the way it is, I can’t justify putting that much into a car. I hear you on the high school money thing, there’s a lot of people able to buy new (and close to new) trucks, and they’re not cheap.