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Tough call.

In your shoes, I might ask the Scout dealer what they'd offer in trade for the Dauntless as is. That would be one datapoint.

As for repowering, would you consider another brand? If you went with a Mercury 115 Fourstroke, not only would it be lighter (359 lbs) than the Yamaha 115 but it would also be cheaper. I would think you could put a Merc 115 on your boat for darn close to $8K. That engine has a very good reputation.

No matter which brand you choose for a repower, unless you plan to keep the boat for a long time don't expect to recoup your investment. We repower older boats (not that yours is all that old, though) for the benefits of having the new engine -- not because it makes financial sense, usually.