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I own a Supersport 15 and have spent a good deal of time in an Outrage 18 and a 170 Montauk, and also towed and launched them all many times. I would not tow an Outrage 18 for any distance behind a minivan, but the 170 Montauk would work fine. With 2 adults and 3 kids I think the classic Montauk 17 will feel too small in a very few years, but the 170 will have more room.

The challenge with a 170 will be finding one in your budget range. It will be easy to find a Montauk 17, but it's not a bargain if it won't work for you, and in my opinion it will not. An Outrage 18 can easily be found for those prices, so is upgrading the tow vehicle and getting an 18 an option?