I've built a Chesapeake 17 and a Pygmy Osprey Standard. Both are great boats. They seemed about equally difficult to build. The slight additional time required for the multichine hull and multipanel deck on the Osprey Standard were offset by the hassle of bending the deck panel on the Chesapeake during installation. I think the Osprey Standard is a little stronger because it has complete fiberglass coverage inside and out. The Chesapeake cockpit is roomier, making it more comfortable for me (5'11", 185 pounds), but my wife (5'8", 125 pounds) prefers the Pygmy. I like the recessed hatches on the Pygmy a lot more than the hatches on the Chesapeake. They are far more water tight.

Both boats handle great on the water. The Chesapeake feels a little more stable because of the hard chine design. I prefer the Chesapeake for fishing because of this. We mostly paddle on sheltered saltwater areas in Maine.

Both companies offer great support over the phone. You can't go wrong with either.