And I'm sure you have thought of it, since you are actually asking the right questions and want to do the right thing - but the important thing is to STAY BELOW the maximums (TW, GVCR, payloads, etc) for LEGAL reasons. Yes, our trucks can (and many do) physically tow more than the printed numbers on our doorjambs, but should you get in an accident (your fault or not), and you were found to be over the specified limits for your truck, an attorney will sue you for everything you have!
I always get the Max Tow pkg to give me more safety (and legal) margin, use a good WD hitch and weigh the setup. Most of us who tow often would be better off with a 2500, but we don't want to daily-drive one of them...so a little more homework on weights has to be done to keep everyone safe. Based on the weights, I'd vote for the GD trailer as well, considering we all load MORE than we think we will! Happy trailering!