My dad was into sailing. First a 19' Chrysler, then a Cat22 ... a J24. When he turned 80 they sold their lake place and donated the boat. But he couldn't let it go and some guy sold him a Cat 25 and delivered it to a slip he found at a nearby lake. But we found nobody wanted to try and tow it because it had a fixed keel and rode almost 15ft high. He had to get some guy with a bulldozer to take it from the storage place down to the boat ramp every season.
A good thing he enjoyed painting because that's how he spent most of his time with it.
I'm more apt to put a kayak on my roof than tow a trailer but it still adds drag. I know how it is moving stuff. And sometimes you have to. But from now on I'm going go with a U-Box or similar if at all possible.
Moved in Oct with biggest uhaul I could get. I rented their flatbed trailer and put my CX5 on that. 12 hours on the road getting maybe 5 miles to the gallon doing 50-55 mph lmbo. I wanted to do the Uboxes or PODS but with moving expenses, I sucked it up and saved several thousand dollars. Next move? Nope. I’m splurging on movers and a service.