I've driven a 22R-E powered XtraCab with a WilderNest for years now.
I'd consider paying this kind of money for a low mile and truly rust-free truck of this generation. Yup, it's kinda high, but nice ones are hard to come by and they are my favorite generation. So they are starting to slip into that collectable region where price and value are not just a straight blue book number. An average one will be much more beat up, have a ton more miles. So what constitutes the high end of the market will be what someone's willing to pay.
To me this generation is new enough but not too new. Nothing said is wrong, they are slow especially relative to modern cars, the doors don't slam with authority and the interior is spartan put kindly. However they are simple, reliable, easy on gas, still easy to fix but modern enough to have EFI (this is huge, no worries about cold weather starts or changes in altitude). The frames are absolutely stout, make the Tacoma that replaced it look ridiculously light duty. These are rated 1 ton in many countries. Is it the same as a F350? No, of course not. But for a small truck there is just about nothing you can do to break it. Beef up the springs and slap as big a camper as you're willing to tolerate the highway speed hit, the truck won't mind.
The advantage to me is that I paid $5K for my truck 15 years ago, it's been paid off several times over and so I worked a lot less than my fellow wage slaves, thus if it takes me 2 days instead of one to get back to St. Louis to see family or an extra hour to get to Moab or Durango, so be it I have the flexibility. We take 2-lanes and stop to take in stuff a lot, too. Lunch at out of the way diners and parks. It's all about the journey to me, so the lack of power and speed is of no consequence to our requirements.
