I've been aboard Morgan Out Islands since 1973 (Trivia: an Islander is a different boat & there are no Outislanders). My 41' ketch has served well as a home to raise our two children from infancy to departure as adults. Charlie Morgan stated, " the Morgan Out Island was designed to moter well for the charter trade". The shoal draft and ketch rig limits performance close to the wind and directly downwind, but the vessel sails very well at other points in 15-20 kts winds. We regular cruise from Maine to the Bahamas with great success. There are compromises to all your choices and few right answers.
I also think very well of the gulfstars and in many ways they are similar to the Morgans. 'take care and joy, Aythya crew