I just bought a Beneteau First 38 for the reasons you mentioned and it was about 10K more than the boat you are thinking about getting, plus it has new 16,000 btu A/C, hot water heater, and reefer, new sails, all the electronics and a swim platform with shower. The point is...... There are deals to be found out their. The Pearson has not got very much room but enough for you and your Chick. I would much rather have a sloop
rig also but the 365 seems to be in well cared for shape. Good luck and see you in the Islands.