As said with a toad I would definitely leave it on. I've found that lowering jacks while on at C.G. will eliminate all sway, again while on truck. Some unhook their tie-downs, others don't. If I stop (rest area, Craker,etc..) for a quick stay sometimes I lower my rear jacks to JUST touching the ground, (careful to not lift truck) to take out the sway. I've been towing Rv's & CDL trucks for over 40 yrs. and I still sometimes get frustrated with my T.C. Try going to a big parking lot with striped lines out in left field using the lines as a guide to get better at backing under your T.C. Enjoy your trip.