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Of the choices you listed, go for the Grady White.

The Montauk 170 and 190 series is more of an Inland vessel and can be rough riding in chop.

Now, if you want to bump up the Whaler model to the Outrage 190 then I would take that model over the Grady.
https://www.bostonwhaler.com/family-o...0-outrage/

I'm sure you will probably get many more opinions.

Try and take a test ride in the Grady 180 Fisherman and the Outrage 190 and see for yourself.

You might also consider the 1996-1999 Outrage 17' II model if you can find one in Hawaii.
http://www.whalercentral.com/userphot...album_id=4