Even though it may look like big water, it fishes a lot smaller. No matter how big the blow, with all the islands, bays and inlets there's always a calm spot to get out of the wind. As long as you stay within Whalesback Channel (and there's no need to go further) there really aren't any long stretches of open water for big rollers to develop. I would certainly feel more than comfortable in a 16 ft tinner regardless of any wind.
We never had a problem finding fish...if you have Navionics, finding weed edges, extended underwater points and offshore reefs shouldn't be a problem. In fact, the owners provide you with a map with lots of fishing spots marked (and hazards) and are always helpful in putting you on fish..