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Go with a 17 Montauk. I have a Montauk 150 with 60HP which I think is a little small for 3 or more people but that's what the Admiral wanted as it was easy to handle. I've heard that my 2008 Montauk 150 weight almost as much if not more than a classic 17 and therefore doesn't really rides that bad.
That said I would go with the 17 foot Montauk as the room is so much better than the smaller one. A 15 sport will be light and un-comfortable. The difference of driving 5 hours in an English short wheel base sports car to driving the same amount of time in a long wheel base American sedan.
I've handled the heavier Montauk 170 by myself and with some wind or current it is a handful like your Outrage 17 to launch or take out.
If you want easier, go with a lighter boat than your current Outrage = Classic Montauk(17) or modern Montauk 150