Thanks for the reply, Banshee! It's great to have THE dev for this section reply!
In Double Clutch, page 127 Trailers and Sidecars section, the last paragraph says
If you want to know if a vehicle can fit in a trailer or be towed, just compare the size class. A trailer can contain a vehicle that is at least one size class lower than its own.
This leads me to believe a size 6 boat needs a size 7 trailer to tow it. However, the trailer size goes from 6 to 8 (same book and page), with with Space column figures not allowing for an intermittent (size 7) option. Logically, this means the boat needs the size 8 trailer instead of size 6, due to the required size reduction.
Of course due to the rule you quoted (the trailer needs to be one size lower then the vehicle) and a full sized truck is size 8, we would need a tractor/trailer to tow a 16ft (5m) boat without penalty.

I guess the solution might be to add the intermittent sizes (7, 9, etc) or change the rules to make no handling penalty for the same size (or lower), the handling penalty for a trailer that is one size larger, and the no towing for a trailer two (or more) sizes over the vehicle.
Of course, a great way would be to simply add a column in the vehicle stats indicating what size trailer (load) each vehicle can tow. For instance, the Eurocar Westwid probably can't tow anything while the GMC Grizzly could probably tow one size larger than it's size, both due to engine, transmission, weight, wheel base, and suspension. This keeps a little bit of crunch while keeping the simulation to a minimum.
I love the Space and Size entries in this edition, BTW. It helps understand what a vehicle can carry, should something "unusual" need to be hauled.