Of these 3 boats ...??????
All three are your basic inexpensive ways to go cruising. All three are reasonably well constucted with the Pearson being slightly better built than the Morgan and the Morgan slightly better built than the Hunter. All three are pretty simply constructed and crudely engineered.
Of the three I usually eliminate the Pearson 365 from my recommendations because they are painfully slow (PHRF 207-234) which is the range of speed normally inhabited by the better 22 foot trailerables) The Morgan 38''s and Hunter 37''s offer similar speeds to each other and are significantly faster boats than the 365(Morgan 134-141, Hunter 132). This extra speed means less motoring and more sailing and faster passages which is improtant in Florida where offshore legs can be pretty long. Also when you are looking at boats this size which have slightly smaller fuel and water tanks than a larger boat, the ability to sail more means less frequent fuel stops. This is partially offset by the 365''s bigger tankage and smaller engine. (BTW 30 hp is a little on the lightside for a high windage 17700 lb boat)
Of the three choices, the later Hunters were actually the nicest finished and laid out, but there were details on these boats that were less than perfect and should be looked at pretty carefully to see if they have been corrected. Steering gear on the Hunters (especially the earlier ones) have been mentioned.
All of these boats are going to be roughly 20 years old. That is something of a magic age for a boat where a lot of original installations will need attention if the prior owner has not done the work already. To repeat my old boat litany, you can expect to find some ''issues'' with any boat this age. Unless very well maintained and updated by a previous owner, you might expect to need to address some combination of the following items:
∑ Sails, chainplates, mast step and associated suporting structure, standing and running rigging that are beyond their useful lifespan,
∑ an engine that is in need of rebuild or replacement,
∑ worn out or out of date deck, galley, and head hardware,
∑ worn out upholstery,
∑ Out of date safety gear
∑ electronics that are non operational, or in need of updating,
∑ electrical and plumbing systems that need repairs, upgrades to modern standards or replacement.
∑ Blister, fatigue, rudder, hull deck joint or deck coring problems
∑ Keel bolt replacement (bolt on keel) or delamination of the hull from the ballast for a glassed in keel.
∑ And perhaps a whole range of aesthetic issues.
To a great extent, your ultimate choice might easily depend on the individual boat and how she was treated by the prior owner.