Your log-on name makes me wonder if you are indeed located in EauGallie, near Melbourne, FL. If so, having a masthead height that allows you to get under the 48'' RR bridge E of the Port Mayaca Lock, and therefore allows a fascinating cruise across Florida on the Okeechobee Waterway, is a criterion in boat selection I''d recommend to you. It should be no problem given your size preference.
Pearson 323''s were designed along the same lines
as her larger sisters, the 365, 424 and 530 (the latter ones mostly being ketches but with some sloops and cutters thrown in). Because she was the last design introduced, the ''European'' design style was adopted and she therefore looks a lot more modern but she still has relatively shallow draft and what at the time was considered comfortable, largish beam for her length. I don''t think the layout suits a visiting 2nd couple, but perhaps you have close friends in mind for whom the layout wouldn''t be a problem.
Personally, I like the boat''s simple lines
and functional deck and cockpit. It is certainly capable of going all the places you mentioned and is in fact a good choice for cruising the Bahamas. The boats built by the ''old'' Pearson (I''m excluding the stillborn attempt to reintroduce the company in the late 80''s) were generally considered to be strong boats, well constructed for the price.