Just checked a few local dealers.
Few questions for you:
Scale of 1 to 10, how important is
the v8 engine? (could a v6 do job if price is right)
a legit 5 or 6 liter engine? (a lot of the Chevy/GMC models use the 4.8)
a model from the past couple of years? (go back '05-'07 and prices look sweeter)
standard vs. automatic? (preference for either)
the interior space you'd get with extended/crew cabs? (could regular cab do job if price is right)
the truck bed? (do you need that open storage or could a truck-based SUV work out)
brand? (Chevy, GMC, Dodge, Nissan, Toyota)
The first few to jump out at me using the original criteria were these (all extended cab):
'08 Chevy Silverado 1500
4x4 auto
4.8 v8
31,680 miles
$21,605
'08 Chevy Silverado 1500
4x4 auto
4.8 v8
46,668 miles
$21,645
'08 Chevy Silverado 1500
4x4 auto
4.8 v8
69,187 miles
$21,845
Keep in mind, those are posted prices. I didn't make any phone calls. Getting them for $20,000 off the lot, all fees included, isn't impossible. Not even up here in truck country.
There's always that deal to be had, too. In last weekend's paper, a dealership 3 hours south of me started advertising an '05 GMC Sierra 1500. Extended cab. 4x4. 4.8. V8. A/C. Auto. 9500 miles. $18,990.
If you've got an eye for trucks I'd definitely look at private sales as well. Another amazing deal was in the classifieds of the same paper. '05 GMC Sierra. Extended cab. 4x2. 5.3. V8. A/C. Auto. 36,000 miles. $15,000. With a whole lot of extras included (LED exterior lighting and lots of chrome additions). Nearly flawless condition.
+shrug+
I'm trying to make a truck/car (preferably truck) purchase this spring for under $16,000. '03-'05 has been my sweet spot.