Why would a Jeep have trouble towing a TheMightyHobie18? My first car was an '89 Wrangler. I bought it specifically to tow my catamarans and be able to beach-launch without getting stuck. I couldn't even feel the boat and trailer behind the Jeep.

Not long distance, but I've towed loads in excess of 6000#s with my '89 Comanche, which has the same drivetrain and gearing as the Wrangler

They were both 6-cyl manuals. If your Jeep is a 4-cyl it might be a little different...