One of our club members tows with a 1999 or 2000 Chevy 1/2 ton truck, I believe it has the 5.3 V8 with a automatic. It's a short bed and a extended cab without 4x4. He has brakes on both trailer axles, and I strongly recomend the brakes. He has towed his YJ on a tandem trailer to Moab 3 times, numerous 4 hour trips, and we just got back from a 1,300 mile trip. All these trips start in central Illinois. (19 hours to Moab).
His truck has 215,xxx miles and he does a excellent job on maintence. He has not had any problems on any trip related to pulling his jeep on a trailer.
He has had problems on trips, AC went out on 1 trip to Moab, had to replace a PS pump this year, and his fuel pump went out on a trip to Arkansas last year. Like I said, nothing related to towing.
A side story.
Be prepared. The fuel pump went out 3 hours from home, we limped into a rest area and Diagnose the problem. Yep, fuel pump.
How we fixed it.
One friend , who we were meeting on the road was a couple miles from a NAPA, he picked up the pump . Myself, the trucks owner, and 1 other club member cut a square hole in the bed of the truck using my Honda generator, and a 4.5" grinder with a cut off wheel from the other member, long story short, 1.5 hours later we were back on the road. BTW , it was 95* with no shade.
One other thing, he does use a load equalizing hitch.
1957 WILLYS pickup,
1973 J 4000,
1978 CJ7 DD.
1979 CJ7 360, TH400/Quadratrac.
1980 CJ5 trail Jeep.
1989 YJ the CJ to YJ.