I tow my 18' boat with my '96 Roadmaster, LT-1 V8, trailer towing package
What do you have for a hitch?
As far as what I'm going to be towing, it'll be a variety of cars. I do Picture Car Placement for films and other productions. Typically the owners of the cars have their own trailers and don't want to let their babies out of their sight. But once in a while someone will just lease their vehicle to the production for the run of shooting. So it might be a Model T, it might be a 2012 Camaro. If we need multiple cars, we just bring in semi or a fifth-wheel. But it's not uncommon to need to just pick up one car. The wagon would be great (if it'll work) because it's a Grandma/SoccerMom-mobile and can "work" even when not being used as a tow vehicle, whereas buying a dedicated truck for perhaps three uses a year would suck the profit out of the job for several years. Especially if I bought a truck that could also be used as a people mover. The Roadmaster is already here and paid for.
Naturally, if it's a '74 Eldorado or a Shelby Cobra or some other exceptional vehicle, either in size or value, we'll make appropriate arrangements, but the bulk of the tasks in the last couple of years would have been a Model A, a '30s coupe, a Gremlin and a Toyota Camry. So, as I said, it varies.
I'm sorry to get people so far off the aquatic focus, but there's not a lot of info out there on the subject, and boaters at least think differently enough that you'd have an idea, compared to my flat-out guessing!
Many thanks!
~ Michael