I've got a bit of a delimma. I've exhausted myself trying to think over the possibilities, and would like to get some external input. This is not a chevy vs dodge vs ford thread. My situtation: We own a landscape architecture and landscape contracting business. We have always run chevy trucks, our newest current fleet purchase was a 2011 2500hd 6.0 gasser. We have several different kubota excavators, bobcats, kubota tractors, etc. Currently, our heaviest equipment weighs about 6,500 lbs and is pulled on a 10,000 GVWR bumper pull trailer. Recently, we have been getting into pulling heavier loads much more frequently with the 14,000 GVWR dump trailer. For simplicity of maintenance, we have always run gas trucks but getting into the heavier loads, the benefits of a diesel for daily towing are starting to look better. Here is my delimma. We are intrastate only and correctly licensed to haul any truck and trailer combination up to 26,000#. However, we would like to stay under CDL which means the heaviest duty truck I can get with the trailers we already have is a 3500HD SRW Duramax at 11,400#. This truck will also be needing to tow a single wheel tandem gooseneck to haul a larger kubota excavator which weighs in around 10,200 lbs. I don't want to get a truck that handcuffs my ability to haul the equipment I need, but I want to draw on the expertise of some who have towed goosenecks. Between the 2500HD and 3500HD similarly equipped, towing is identical. With the 2500HD, my trailer GVWR can be 16,000# to stay under CDL, with the 3500 HD it would have to be 14,000#. Both trailers can support the weight, but the 14,000# is closer to the max load without a higher pin weight. The 16,000# trailer can more easily bear the load but with a 2500, the pin weight would have to be lower. Basically the question is this: Higher GVWR truck with lower GVWR trailer (3500HD SRW and 14,000# trailer) allows more weight on pin , or Lower GVWR truck (2500HD and 16,000# trailer) requires more load weight on trailer itself. What would be my better option? I see plenty of hot shot drivers with 20-24k# GVWR dual tandem goosenecks behind 2500s but is that ideal and can the truck handle it?