All good suggestions here, I tow a Wrangler as well. I keep my rear camera on so I can keep an eye on it. If not I would forget it's back there. Really tight turns are the only time you will have to worry about it. I can get in and out my subdivision with not problem and those are the tightest turn I have ever encountered.
DO NOT BACK UP WITH THE TOAD.
I hope all your coordinating works out for you, that's a hectic schedule, good luck and enjoy the ride.
2013 Berkshire 390 BH
2013 Berkshire 390BH