Re: Towing with 04 Jetta Wagon TDI
"Small" cars, especially newer ones, are a lot bigger and heavier than some people seem to think. The curb weight of the Jetta is nearly 3000 lb. Weight ratio wise, towing 1500 lb with a Jetta is no different than towing 2500 lb with a half-ton pickup. Nobody thinks twice about towing 5000 lb with a truck, so why is 1500 lb "way too much" for a vehicle that is more than half the size of the truck?
As for sway, the car will be able to handle the ~150 lb of tongue weight needed to prevent sway unless you're in the habit of stuffing the trunk to overflowing with heavy gear. If you use electric brakes, you can apply the trailer brakes without applying the tow vehicle brakes, which will bring things back in line if it does start to sway.
The biggest issue (assuming you don't do something silly like try to tow without trailer brakes) will be launch and retrieval. I tow a similar sized boat with a car, and the first time I tried to launch I backed up until the front wheels were almost in the lake, but the boat was barely deep enough to be able to start the motor. I had to back up quickly and slam on the brakes to get the boat off. It's a roller trailer too. I managed to make a few adjustments to lower the boat by 4 inches or so, and I put a 5 foot tongue extension on the trailer
(see here). That solved the launch problem.
Retrieval can also be challenging. Try to avoid extremely steep ramps and less than optimal traction conditions. If the lakes you want to go to have paved ramps with moderate grades you should be fine. Otherwise, look for a bigger and/or AWD/4WD tow vehicle. Typical car manual transmissions have a fairly tall first gear, so getting started can be hard on the clutch and may lead to premature failure if you launch frequently.
Silvertip also brings up a good point about the TDI engine. These engines have fairly strict lubrication requirements to begin with, and high heat, high torque operation just makes the oil's job harder. Don't even think about using anything that doesn't meet the VW 505.01 specification.
