Depends on you and mostly on the trail. It's not really even a matter of opinion when it come to being on a Jeep trail, for example.
If you're trying to get down Jeep trails with a 8 foot bed, you might get lucky on some more moderate to easy ones. I got my dad down one in a 350…with no damage. He never did that again, and it was incredibly slow.
The harder trails it just won't happen without trail damage and even on the easier ones, you'll have some guaranteed pin stripping and dragging of your hitch.
On more maintained fire roads and such, you'll usually be fine, though I've been on some surprisingly messed up fire roads too.