Hi Jaque
It sounds like your truck just might be sufficient to pull a 5000 pound Ollie down the road. We also believe in massive overkill in a tow vehicle. We tow Legacy Elite II with a Nissan NVP 3500 making our rig about 45 feet long. Since we picked up the trailer in March, 2016, we have accumulated over 8000 trailer miles.
Suggestion #1: Get the backup camera and USE IT. When I tried backing into the driveway without using the camera I backed into the second story deck and cleaned the camera right off the trailer. Replacement camera was $300. I am also considering side cameras since the monitor will accept 2 wired cameras in addition to the wi-fi camera.
Suggestion #2: Before driving on any gravel or narrow road, disconnect and check it out first. After boldly entering one such road, it took the towing company all afternoon to free first our trailer and then our tow car from a sand trap.
Suggestion #3: Don't always trust your GPS. Ours led us in circles around a development with very narrow streets that we should not have ever gotten into, and down a gravel road with a sand trap at the end.
Len R.