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As has been said, one of the key factors to consider with a repower is local dealers.
While many, if not all, manufacturers offer decent 250/300hp models, dealer service and price should be determining factors.
What dealers are a reasonable distance (<90KM) from you?
It is recommended you seek detailed quotes from multiple dealers that lists the specific items, part #'s and price for each. It is with this information you can evaluate costs.
I would look at Suzuki's smaller 300 and the Yamaha 300. Lots of good feedback out there for the Suzuki and that Yamaha is a proven motor. Both have lot of torque. Both have been around for a while unlike the new Mercury) And both of those motor match up well with that hull. There is a Suzuki 300 video on youtube of a 23' whaler. That video is very impressive and what i have heard about that motor is that is extremely strong.