IMHO, in today's world where bodies don't rot out in 10 years, an older truck, 5-10 years old, or more, with perhaps higher miles is the way to go. Get it cheap, drive it, fix it mechanically, and have a clean title. What's a new tranny rebuild, $1200? Drop in a new long block in a weekend if you need to, etc. Not worth the hassle of checking the frame for cracks, rebuilding, etc.
I picked up my 98 4WD Suburban a few years back, 140,000 miles, driven by a soccer mom. I love this thing. Tow package, 3.73s, 3rd seat, leather, heated seats and mirrors, etc., etc. Great for camping in it too.
Picked it up for a song when gas prices went sick.
Buy it, and drive it today. Not spend 3 months of my time getting it driveable.
Just my $0.02.
Old, noisy, slow, and just generally wonderful. Wheeling Jeep.
Less old, less noisy, less slow, daily driver Jeep.