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I have owned both the Montauk 17 (three of them actually) and the Outrage 18 (owned for over ten years) and they are both great boats. It is a tough call which is the greatest Whaler of all time, the Monatuk or the Outrage.
The Montauk is much easier to handle, the Outrage 18 is more capable being essentially half again as much boat with half again the expenditures to buy and maintain it.
You can tow a Monatuk with anything.
You will need at least a V-6 powered car, SUV or pickup truck to pull an Outrage 18. I used a 3.0 liter V-6 powered Toyota T-100 and an old V-6 powered Nissan Pathfinder to tow my Outrage 18. No problem.