For those that do not remember. In 88 this was the first year for that body style. ALL 3500's were 8600 gvwr setups, ALL 2500's were a 7200 gvwr, and 1500's a 6600 gvwr. THERE WAS NOT a dually in this body style until 90 or 91. The 2500HD came out in 89 or 90 which only had a tbi 350, along with the 8 lug 8600 gvwr. The SW 3500 now had a 9200 gvwr. Then the dually came out it had a typical 10K gvwr with a 7500 grawr.
Then if the OP is correct with WB, a 141 is a 6' bed, if he had an 8' bed as my 88 had, it would be a 155" WB. A BB in 88 had a dana 70, the 350 the Corp 14 bolt rear axel.
Anyway, max gcwr with this rig is 13500, unless he has 4.56 gears, which would put him at 15K. 3.73's would be 12500, and 3.42s 11500. Heaven for bid he has 3.08's, that would be 10500! The chassis will handle a larger trailer, but as noted, with a whopping 185hp, and not even 300 lbs ft of torque, he will be hurting in the power category from a speed standpoint. My 96 Crew cab with a 185/385 6.5 TD and a NV4500 did pretty good with a 6500 lb trailer, total gcw around 15K. but I was down to 35-40 on 3-5% grades in 3rd, ie gear below direct. That was a better towing tranny than the th400 or 4l80E auto setups, no matter the RA in it. 4.10s like I had were the cats meow from a gearing split stand point. If you had the munci 4sp, and 3.42's, your overall low, and high gear ratio were on par with the 4.10 nv4500. Pretty much from a performance stand point, equal.
marty