Re: Freeboard and flair? Bolger work skiff
How much freeboard is right? It's not simple, although a flat-sided skiff for oars or power makes it more straightforward. You don't have reckon the amount of heel under sail.
I've got a Bolger Gypsy, a 15 ft. sailing skiff, with a lot of sheer and not much freeboard.

But the hull has hard chines and resists heeling farther. To add some security, I put in side decks and a coaming. Even so, I've shipped some water on gusty days but never actually swamped.
I sail on inland waters with not much swell and few or no steep wakes. If you use the boat where there's a short, steep chop (e.g. a tidal ebb against the wind) or where there are ferries or other power craft that trail steep wakes, you'll need more freeboard. If your frequent courses put you across the prevailing wind (and swells) you'll also want more freeboard. Same goes for carrying heavy loads, whether people or camp supplies.
That local knowledge is often what separates the experienced boaters from the accident-prone novices.
Good luck!
We're merely mammals. Let's misbehave! —Cole Porter