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Chev/GMC:
You span two different platforms. The 98 and some 99's (Classic) were the 'old' platform, and 99-03 are the current platform. Very different.
The 'old' platform has the venerable 350 small block, and 98-99 would be the Vortec SFI..... bulletproof, although they can leak oil from the intake and oil cooler lines. The brakes were always rear drums, but I have never had problems with the rear ABS. The extended cabs were available in three-door or two-door. Rare to find a 1/2 ton ext cab longbox. That's a big truck! If you are considering 3/4 ton, you will find that bodystyle through 2000. All of those fuel pumps are noisy, but they stay noisy and don't always fail. Look for leaking front axle seals... the left hand one costs $$$ in labor. My personal experience was with a 99 Suburban (same basics) that had only an alternator and u-joint in 127,000 miles.
The 'new' platform is the 'current' (99-2006). They generally have the 5.3L V8 based on the new Gen 3 LSx architecture. Great motors, lotsa power.... iron block, alum heads, plastic intake. No real problems, but some of the early ones had audible piston slap. '99 was all three-doors, '00 was three-door or four-door, and 01-newer were all four-doors. Try to buy a 2003 as they had some minor changes.
Dodge:
The Dodges from 98-03 also span two platforms. The 98-01 were the old square trucks with the 5.2L (318) or 5.9L (360). Both are gas pigs, but engines that have been around forever. Intake leaks at the back of the motor were common. Those trucks also had solid coil-sprung front ends that were strong but unsprung weight was huge (GM had torsion-bar IFS). 98's were two doors, 99-00 were either two or four (Club cab or Quad cab) and 01's were almost always four-doors (suicide rear). Rear ends were certainly a weak point.
The 'new' Dodges '02-current are crew-cab-like, but the length of an extended cab. The rear doors open like a car, not suicide like earlier Dodge, GM, or Ford. Motors were a mix. You could get the 4.7L SOHC V8 that originally came out in the '99 Jeep Grand Cherokee or the old pig 5.9L (360). The 4.7L isn't quite enough for the big truck. In 2003, Dodge answered with the 345hp 5.7L HEMI. They have proven to be pretty good trucks.
My two cents: Either buy the best-cared-for highest-mile cheapest old-body GM as you can find, OR buy the newest Dodge Hemi or GM you can afford.
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