I am an Islander
36 owner. But I have the "Standard". The Freeport
has better accomodations, The Standard is a better sailing boat. (Standard was recognized as one of the 10 top cruising boats of all time by Cruising World) I've been a liveaboard
on mine for better than 9 years.
The skeg hung rudder
(both models) is popular with cruisers becaue of the protection it offers.
I understand from a former dockmate who worked for Islander
that boats built in '75 and some time later had blister problems due to resin compound changes. I dodged the bullet there. Mine is a '74.
Hope this doesn't set me up as a target here.