I recommend following the state law as a minimum requirement, but in many cases, it makes sense to be overly conservative.
A lot of trailering safety is about stopping distances. Your stopping distance will be significantly greater with a trailer with no brakes once the weight of the trailer is more than half the weight of the tow vehicle.
My usual tow vehicle is a Honda Pilot with a curb weight of 4400 lbs, so I would probably put brakes on a trailer if the weight was over 2200 lbs. In situations where I end up towing vehicles heavier than about half the curb weight, I always leave a lot of stopping distance in front of me, as my experience is that trailer brake systems are not the most reliable things in the world. Even with towing a light boat, I still tend to leave lots of stopping distance as I prefer the rods and stuff in the boat not get thrown around with sudden stops.
The other reason I like a lot of stopping distance in front of me is that I am often concerned with whether the vehicle behind me will be able to stop before hitting the back of my boat. Keeping all my stops slow and gradual are great insurance against being rear ended. Being rear ended when towing a boat is ... ... ... sub-optimal ... ... ... and very expensive to repair. And whether or not your trailer lights are working, the fellow that hits you is likely to claim that your brake lights were not working.
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