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I have delivered thousands of canoes on 6 to 40 hauler trailers. I will do almost anything, including triple stacking to keep from dealing with a trailer.
An engineering type, I do not understand the electrical lighting problems endemic to trailers, but have spent lots of time on my back in the snow/ rain, mud fixing same.
Trailers compromise parking, even turning around in some places.
Trailers can tip over in extreme cross winds. So can SUV's but the latter has never happened to me.
As per PRG51 below, wheel bearings are another, constant, issue, but Bearing Buddys and a grease gun go a long way towards solving that one.
We spend several thousand dollars and engage title and licensing, lighting issues when we must because we're hauling a significant number of hulls for a camp, college or manufacturer. I need to be paid to haul a trailer.
To haul a couple, up to four hulls? Get a long combi like my late, lamented Saab, a BMW/ Audi/ VW/ Subaru station wagon, save money and frustration and simplify your life.
My 4'-11" daughter has a small hatch back and halls an 18 foot sea kayak on it at times and other times canoes.
She has no hassel with any extra registration, insurance, parking, wheel bearing maintenance or trailer storing, and is very happy with her set up.
I have a Ford Escape with a hatchback, and carry two sea kayaks and one canoe
With all that said, I imagine it is a lot easier to load and unload off a low trailer
1. Keep the bearings greased; make it easy by having grease fittings (Bearing Buddies) on them, and you can grease both wheels in a few moments. And make sure you use WHEEL BEARING grease intended for high-temp applications (small wheels rotate faster for a given mph than big wheels do).
2. Keep the tires up to pressure. This means not airing them down too much, as so many advise. With such a light load as kayaks, you don't need to put the maximum pressure in them, which might be 65 to 80 psi for some tires. But you also should not let them go down to ridiculously soft pressures, because that causes overheating of the tires and uneven wear. On the Trailex SUT-350-M2 that I tow, the tires are the little ones with maximum pressures in the 60+plus psi range. Yet the trailer maker's decal says to use only 20 psi. I never go that high OR low and have had no trouble with hauling glass kayaks. I've put anywhere from 35 to 50 psi in them and settled on 38 psi. Tires are wearing normally and the ride is soft enough because of the soft leaf springs on that kayak-specific trailer.
Those are the two things to pay special attention to. But really, watching tire pressure is something you should do with your car anyway, so there's only one extra thing to watch for: adequate grease in the trailer's wheel bearings. And that is incredibly easy to do.
Now, for the bugaboo that you cannot control: In Colorado, tolls for trailers are extremely high. It wasn't always this way; things changed a couple of years ago and C470 Authority began gouging trailer users. It's based on number of axles, not actual weight or length. So my combined truck and trailer and payloads add up to less weight than a full-sized SUV with 1 driver and no passengers or loads at all. Go figure! But I sure wouldn't let extra toll or parking charges deter me from buying a trailer if it was better in other ways. (And C470 Authority and their incompetent recordkeeping can go stick themselves where the sun don't shine! Good riddance.)
To my way of thinking, I haven't seen any "bad advice" here at all. Trailers aren't right for everyone, and your arguments in favor of trailers over roof racks sound more like a statement of "my way is right" rather than logic. Lots of other people said they prefer trailers, some of the time or all of the time, but in most cases also stated some logical qualifiers.
As far as your reasons for trailer use being so universally correct, they aren't. For one thing, "no overhead lifting" is no reason for a non-disabled person to use a trailer if instead they could use a bit of imagination and ingenuity. I've been loading boats on roofs all my life, sometimes with boats quite a bit heavier than canoes or kayaks, and sometimes on full-size vans. I'm not exactly big and strong, but I AM totally intolerant of doing things the hard way, and know how to modify a rack and my loading technique to make the job easy. If you are actually reaching above your head while lifting the entire boat, you are doing it the hardest possible way, and the logical thing to ask yourself is "why do it that way"? If you don't have the ability to modify your rack to make the job easy, then using a trailer may be a good choice for you, but it's not the only way to make boat-loading easy.
As far as bouncing goes, any trailer you buy which is not specifically designed for ultralight loads is likely to have this problem, and virtually every cheap trailer will. On such trailers, you'll have to modify the suspension yourself. If you buy a nice trailer (such as special one for bikes or boats that has a nice, soft suspension), it will cost the same putting roof racks on a small fleet of cars. Even with a cheap trailer, you still have to put a rack on it, and the rack will still be fairly expensive if you can't build it yourself. Besides, the OP is only looking to carry one boat.
As far as having the boats "already loaded", that's nice if you have a place you can park a loaded trailer. Not everyone does. I eliminate the inconvenience of loading boats by making my boat-storage methods quick and easy to use. Even my biggest, heaviest boat can be gotten out of its rack and onto the roof in about three minutes, and then all I have to do is tie it down. I don't have to do any heavy lifting at any point in the process on account of the way I designed my storage systems.
You say you can walk a trailer anywhere you need, but that's true only for you, not everyone. Try doing that so you can turn around on a dirt road or a back-woods road that's really steep. It'll take a team of helpers unless you bought one of those terribly expensive specialty trailers, but even then, you are wasting time that you wouldn't have to if the boat had been on the roof.
Overall, I'd say the pros and cons of trailers versus racks have been well described. As many others have said, I agree that which is the better choice is not universal, but depends on the specific situation.
I was referring to the expensive trailers. I figure Sports Rig trailers must be a couple thousand bucks at least, since they seem to go by the policy, "If you have to ask what it costs, you can't afford it" (in actual fact, I think Sports Rig is on the verge of going out of business, since NOBODY closes their website for several weeks just to "take inventory". Who believes a company that small has an inventory that can't be tallied by one person in a day or two? A less-cynical interpretation might be that it's such a small operation that if the boss takes a long vacation, everything comes to a halt). Anyway, I think I spent $200 (MAYBE it was as much as $250) on my roof rack, so yes, I think I could have bought racks for 8 or 10 cars ("a small fleet") for the price of a Sports Rig, but granted, I carry canoes and similar boats gunwales-down, so there are no expensive accessories. I'm thinking of replacing it this winter with one that's home-built from the ground up, which would have been the smart thing to do right from the start.
As to the mileage penalty of boats on the roof, I myself wouldn't use it to justify a trailer. A quick calculation using some rough mileage figures of my own, with and without boats, shows that at $4 per gallon, I'd need to carry boats for 110,000 miles under average conditions before recouping the cost of a Sports Rig (assuming it costs $2,000), and 50,000 miles under the worst possible conditions (high-speed driving into very strong headwinds). In any case the estimate is conservative because it's based on the unrealistic assumption that carrying boats on a trailer would not affect mileage at all. I'm not sure I'll ever reach 100,000 miles of driving with boats on the roof. However, if the price of gas goes up enough, especially if it were to force me to use a much smaller car, it would take considerably fewer miles carrying boats to recoup the cost. Therefore, it seems that for a small-car owner, a really "nice" (expensive) trailer starts to look pretty darned appealing.
I have a standard boat trailer that has about the lightest suspension you normally see on such trailers. It carries a load that I think is somewhere around 400 to 500 pounds, and until I removed one leaf from each spring, it bounced terribly on any kind of "abrupt" bump, even small ones. The outboard motor used to bounce all over the place, and since the motor itself weighs 100 pounds that created a separate problem in itself. I finally got the bouncing under control though. Besides removing one leaf from each side, I built a bracket that removes all movement capability from the outboard motor's mount while in transport, and I put less pressure in the tires than recommended, so that they have about the same amount of "squat" as they would if at normal pressure when carrying the load they were actually designed for. However, running the tires with a lower pressure requires an additional modification - you must install an inner tube since they don't always remain sealed tightly to the wheel, and once you lose the seal there's no way to re-seat the tire with normal tools. The inner tube eliminates the risk of getting a non-repairable flat due to a bad seal.
Sure, you are correct that your boats won't be "beat to crap" as long as they are well secured, but I still haven't seen a trailer built from one of those kits that isn't sprung WAY stiffer than what remotely makes sense for carrying paddle craft, and they do bounce badly. It seems that people's tolerance for impracticality is inversely related to their understanding and ability to make things better, so yes, you CAN carry your boats on a 1,000-pound suspension, but plenty would chose to do it differently.
By the way, a guy in our local paddling club has a custom-built trailer for hauling multiple boats. It too is way heavier-duty than needed, but instead of the ultra-cheap, lightweight axles, tires and springs of kit trailers, it uses what I'd call a "real" trailer axle that's not made from stamped sheet metal, and the tires are as large as those found on something like a minivan, and the springs are far larger than what you see on any kit trailer. The longer leaves and progressive action of the springs provide a much smoother ride, and that combined with the relatively heavy weight of the trailer and the larger, cushier tires eliminates the problems associated with cheap trailers and their typical suspensions. It's a perfect example showing that there's more than one way to skin a cat, and that you get what you pay for.