I tended to take that Four Winds into places where I shouldn't have gone, and and a result, ended up high-centering it on more than one occasion. Two of those occurrences were on the same trip - the first, I was able to dig my way free, but I needed help on the second one. I solicited the help of a Toyota pickup owner who didn't think he could help me. It didn't take much, but we were free again.
Take your time, learn your rig and enjoy! You'll become accustomed to the attack and departure angles that cause interference, and how to approach similar ones in the future. I learned to pull in at an angle rather than head on, if at all possible. Sometimes it became a game - are we gonna drag the tail? We'd slow down to lessen the impact, and more often than not, the tail wheel did its job.
This unit had big casters on the hitch, one had been damaged by the previous owner. They were anchors, in my opinion, not helpers. That's why I went with a single roller that didn't hang down. Granted, it got slid sideways on occasion, but it was a rolling slide. It helped a lot.
I should post my "9 disaster trip" story again one of these days - RV.net seems to put inactive threads in archive after a year, then purges them. My older posts are long gone.
With the combination of fully inflated airbags on the rear axle, helpful roller(s), and driving technique, you'll do fine.
Enjoy!