Stop in for a cup of coffee

so, do I really need a 3/4 ton? trailer is 3000.. car is 3050 - my 1500 has a tow rating of 7500, that leaves me 1450.. add in a generator and some tools etc... even if you call it 1000lbs worth of "etc" stuff - I would still have an "unused" 500lbs or so of towing capacity left... or is that pushing it too close?
As someone who has towed a **** ton and who has a cdl, I advise against trying to tow that kind of weight with a half ton. Powerwiae you'd be fine but weight wise the gap is too much