The description in the upgrade package includes "JBL Audio". The description in the premium package includes "Premium JBL Audio". That tells me the audio systems in the two packages are different. What the specific differences are, I have no idea.
I will be coming from a two-door Jeep Wrangler on 35's with a 3-inch lift. Departure angle has rarely been an issue for me. With the new Tacoma, the clearance concern for me is the spare tire which appears to be way lower than the hitch.