The 29 foot trailer is probably a longer LEVER than is safe with a short wheelbase Grand Cherokee .
The boat OTH would be fine .
Why , you ask ?
A boat has the engine at the stern .
for that reason a boat trailer has its axles near the back of the boat .
the longer distance between the hitch and the axles make the boat trailer much more stable .
The travel trailer has the axles much closer to the hitch .
The trailer length behind the trailer axles is uncontrolled weight exacerbated by the LEVER principle .
For that length of towed vehicle I would want a longer wheelbase tow vehicle .
