For sure don't exceed the tow limits, or overload your rig.:redneck: I'm towing about 6K with my trailer fully loaded. My truck is rated to tow like 8900. I have brakes on both axles, and a good controller. I don't plan on towing more than that anytime soon. If you are considering towing a jeep, get a light trailer with good brakes, and you should be fine with an older 1/2 as long as you don't want to go fast. BUT if you can get a nice 3/4 or 1 ton for the same price, go for it. My decision to go 1/2 was based on this:
I use the truck for DD, baby hauling, home depot loads, tow my rig to the trail, don't plan on using it offroad,
2006 Sierra Denali Crew Cab Fully loaded, DVD,2 tone leather, plush insides, all wheel drive(not 4x4) 6.0L 29k miles, factory warranty, 1 owner, tow what i need $23K blue booked at 31K
2001 2500 90K miles, 6.0L, bare bones almost work truck, dings dents etc, tow what i need, but still a 6.0L $20K
2004 2500HD duramax crew cab, bare bones cloth, no sunroof, nothing, 80K miles, no warranty, higher fuel cost, more maintinence, DURAMAX/ALLISON tow anything.$33K
2006 2500HD all the bells and whistles, low miles, warranty, etc. $43K
for you:
1999 1500 Z71, low miles, clean, maintained, extended cab -$4500
1999 2500/3500 crew cab, clean, maintained, low miles-$9,000
1990 3500 454/TH400 high miles, beat to hell, works like a champ-$2500
Just don't buy anything too crappy that you'll need to dump $$ into or else in the end you could've bought the better truck to start, and skipped doing all the work, and wasting your time.