We've towed a 2619 with our 02 Honda Odyssey for approximately 14,000 miles with no problems but I have to admit we are thinking of upgrading to a more capable TV. I should also mention that it's just the two of us and we remove the 2nd and 3rd row seats and limit what we carry to stay below the combined Ody+TM weight (GCWR) allowed by Honda. My personal opinion is that you'll be OK if you stick to the short trips you described, weigh your Star+TM loaded to make sure you are within GCWR and drive cautiously. If you haven't towed before you may be thinking in terms of whether you can make it go but the real problems come in when you need to make it stop. Everything will feel normal braking at 30 MPH but you will think your brakes have failed the first time you try to stop from 70 MPH. Leave twice as much room ahead as you normally would and don't be surprised when people pop out of side roads because they want to avoid getting behind you on two lane roads. And yes you need a WDH and transmission cooler. Just my $0.02. One other item I didn't see mentioned above is that a WDH transfers weight from your rear axle to both your front axle and your trailer axle(s). You'll want to include that info in your loading calculations.
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