buying first boat
I am sure there is someone who knows the Pearson well and can respond. But it is actually pretty illustrative of my advice above. The Pearson 365 is a 70''s vintage, ketch rigged boat that does not even have a quarter cabin below. Its PHRF is a whopping 210! It certainly is a fine boat BUT... it is dead slow, has the accomodations of a modern 25ft boat and has 1970''s wiring.
I just went through this process in finding my last boat (closed on her about a month ago). I had some objective criteria and some subjective criteria.
My objective criteria:
1980 or newer
PHRF of 144 or below
solid glass hull
38-40ft (I single hand as well)
aft qtr cabin
My subjective criteria:
nicely finished below
high quality build
few owner mods
Price in a certain range
Sail plan (sloop)
Hull form (5ft draft or less, very good rudder construction, skeg if possible)
If you established some criteria like the above... the P365 would miss on virtually all points and thus be easily discounted. The Morgan 382/3 however hits many of the objective points on the list.
There are certainly many points above that people would argue either way. Displacement, cored hull, age, all have many camps. My thinking was that boats older than 1980 will have much less resale value later and may have poor wiring. I personally like a heavier displacement boat. I personnaly did not want a cored hull as they can rot and are expensive to repair, as well as needing expert repair. Solid glass hull repair is easy and can be done anywhere in the world.
Layout and accomodation is subjective but I put it on my objective list as I was decisive in what I wanted. I wanted a private aft cabin for guests. No boat has much privacy but dividing the cabin lends at least a bit more than just having it completely open. BUT... I can tell you that this really increases cost and makes it much harder to find a good boat. If this is not an absolute need for you, then go with a qtr berth. Rig: many folks favor a center cockpit and ketch rig. I found in my sailing and my looking that the CC design took far too much away in the cabin down below and for single or short handing, I find a sloop with its single rig, easier to deal with... and sloops are in general much faster than a divided rig like a ketch. I found the NE PHRF listing a good guide for assessing how fast one boat might be compared with another. I knew I wanted a boat that had a certain amount of speed.. did not have to be a race boat but AT LEAST as fast as a J/30 or Morgan 382 or faster was my thinking (the Morgan 382 was my BASE boat when I began looking, I felt it was good enough for what I was looking for... SO... any other boat had to surpass it to be considered).
Hope this helps.