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Re: Vehicle to tow my boat!
I have the same boat. Bayliner only makes one cuddy model in 19 feet. Mine has the 3.0L Mercruiser I/O. It weighs a little more than what you are saying. I think the "dry weight" is 2,300 -2,400. Then you put gas in it (24 gal tank) and throw in an anchor and chain and gear and add in the trailer weight and also consider what is in your vehicle (all of it counts as gross wt) and you can ballpark your weight. Short of that, you would have to put it on a truck scale like they have at the landfills to get an exact weight.
As for towing it, any vehicle (properly equipped - tow package or equivilant) factory rated at 5,000lbs should be ok. I'll bet your total weight will be closer to 4,000 lbs all together. Personally, I tow with a Jeep Liberty with the factory tow package and it has 4 wheel disk brakes (my trailer also has brakes) - it makes a big difference. It tows it like it isn't there. And the jeep with it's big disk brakes along with the trailer brakes stops it just fine.
As to launching and retreving, I always use 4hi but used 4lo once on an especially knarly boat ramp and never a problem. Even a paved boat ramp can be slimy especially when your back tires are in the water so that is why even using 4hi will put traction to the ground on the front where you will have a better grip to pull you up the slippery slope so to speak..
In the $1,500 range you should look for an old p/u since it will have a full frame (the best for towing and load distribution) and make sure it is 4wd. A little overkill maby, but best suited for towing in your price range and maybe it will be usefull for other chores for you. A full size p/u will also have bigger brakes and since your trailer does not have any, so this is very important in my opinion anyway.
Sorry for the long post.
Just my opinion.
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07 Impala 3.5L VVT (GF's car)
99 Cutlass 3.1L
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