Frank - you shouldn't have any problems if the truck is in good condition for its age. The only aspect of performance I don't like about the '88 Sub is it lacks a tow package. If I've got more than 2 horses in the trailer, it heats up to the point that I need to keep the heater blowing to keep the temperature down. When I haul horses, it is usually over 50 miles one way with lots of hills. The truck maintains 50 - 70 mph with a full trailer with no problems.
I also wish it was a 2500 Sub instead of a 1500 for trailering purposes. I frequently use my Dad's '95 2500 Silverado with the horses, and the 3/4 ton is just a better tow vehicle. That said, he's had to take the Silverado in for service more often than we have the older Sub - and the Silverado has half as many miles on it. The guys took the Sub hunting this year because the '95 has been having intermittent fuel problems and they thought the '88 was more reliable.
We don't do much/any wrenching on either truck ourselves because they are too new and beyond our shade tree skills. Hope that helps.
