My Jeep is a 6 speed, and I've never had a 5 speed Jeep so I can't help ya there.
But the 6 speed is a good trans, first gear is lower than first in the 5 speeds. And the 6 speed is a pretty tough trans.
People complain that the shifts are crunchy, the trans grinds, and pops out of gear. I've found that if you don't shift it like its a sports car it won't grind or crunch, remember its more of a truck than a sports car. As far as it popping out if gear, if you pay attention you can feel when the shifter isn't fully in gear, when that happens just very slightly let the clutch out and it'll slide right into gear.