Yes you can pull that trailer, I used to pull car trailers to the drag strip on the weekends with my Jimmy. Get your self a class IV trailer hitch, I was using Valley Industries (Hitch) GMC Jimmy Trailer Hitch Class IV Receiver Trailer Hitch Part Number: V1181100 Gross Trailer Weight 4000 lbs./Weight Distributing 6000 lbs. http://www.valleyindustries.com/Default.aspx
You may want to also upgrade your transmission to save it from towing. Install a B&M Shifplus electronic shift improver, http://www.bmracing.com/SPECIALS/ShiftPlus-electronic-Shift-Improver-for-GM and also swap out your servo with a Corvette servo. The servo can be replaced in about 30 min and you don't even have to drop the transmission pan, but if your going to tow, you might as well service the transmission oil and filter and have them swap out the servo. The corvette servo goes for under $45.00 and is a better investment then $1,700 transmission repair. GM 4L60E Corvette Servo kit: 8642079 at the dealer but you can get them cheaper https://www.700r4l60e.com/store/product.php?productid=233
Things done on my 1996 Jimmy:
3.73s / G80 / Intake / Vette Servo / B&M ShiftPlus / .490 Boost Valve / Poly Tranny Mount / Throttle Blade Modified / MAF screened removed / HPTuned for 93 Octane, and attitude adjuster to the Mall.