I am pretty new to the TT thing, this is our second summer. This forum has been a gem for helpful information.
Like yourself, I started out with a truck/trailer combo that was nearing capacity. I had a 2014 Ram 1500 Hemi and a 2013 27BH. Towing capacity was around the 80-85% mark, however payload was challenging for me, esp. when I had my dirt bike in the back of the truck when hitched.
The theme you will see is that while you can squeeze in, the level of comfort you are going to have towing is marginalized when you are pre-occupied with what you are trying to make the truck do. There is also a safety element when you are running around at capacity too.
I gave in and got a Ram 3500 with a Cummins (and now I an way over truck'ed
) and the difference in how towing feels is night and day. I am now able to get any TT or 5th I want in the future as the new rig can pull pretty much anything now.
Ultimately, if you can swing it, you are going to be better off with a larger rig to tow your toys.