Re: I Need A Shrink !
I agree with Lew, I'd put in a bit more HP. Say, 350 to 375 hp. Large displacement (400+ cubes) SB Chevy motors can make 375 hp fairly easily. Much cheaper than going diesel.
That 290 drive is heavy-duty stuff, keep it, but add power trim.
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Common Sense is learning from your mistakes. Wisdom is learning from the other guy's mistakes.
Fr. Frank says:
Jesus liked fishing, too. He even walked on water to get to the boat!
Currently without a SeaCraft 
(2) Pompano 12' fishing kayaks
'73 Cobia 18' prototype "Casting Skiff", 70hp Mercury
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