I doubt you'd be the first...garage and ramp capacities are 2,500lb and 122" deep for the golf cart.
We have carried a Smart car (1,800lb+):
Hitch rating is 8,000lb, plenty for the Jeep.
And, the GCWR is 30,000lb and UVW at just over 20,000...so total weight is probably no problem, unless you fill the Outlaw to max GVWR (26,000lb).
Best luck