purchase boat checklist
I am not sure that your question is very clear. I assume you mean, What questions should I ask myself in order to identify the type of boat that is right for me.
When I start to look for a new boat for myself, (or to help someone else), I start out by thinking about how and where the boat will be sailed.
-Will the boat be daysailed, raced or cruised or all three?
-Will it be sailed single-handed, short handed or with a lot of people or all of the above?
-Will the boat be sailed in an area known for light air, or heavy air, or a wide combination of conditions?
-Will the boat be kept for a long time or sell her quickly in a couple years?
-Is a fixer upper OK or would a boat all set up and ready to go better suit my needs?
-Are there aesthetic or other subjective preferences to consider?
-What is a reasonable budget that will not leave me boat poor? Or for that matter, does it matter if I am boat poor?
That starts to set up expectations. To use myself as an example, in my case I daysail, cruise and race and I do single-hand, with my wife,and with the new boat with guests. This lead me to look for a boat that is easy to sail short handed but with room for a bunch of people for a daysail and another couple for cruising.
I sail on the Chesapeake so I wanted good light air performance but I also sail year round so I wanted good heavy air performance as well. This lead me to a light weight boat with an easily driven hull and a fractional rig for maximum flexibility. I expect to keep the boat for a very long time and so wanted a very sound hull but was not afraid of a boat that needed some upgrades.
I don''t have a lot of spare time these days so wanted the boat ready to use but the boat will live behind my house and I can work through and upgrade things a little bit at a time. I have owned traditional boat and modern boats. I wanted a modern boat but one with reasonably jazzy lines. Other subjective issues was that I wanted to have a draft under 6''6", deeper than which begins to limit your cruising grounds on the Chesapeake. I wanted a boat that was a minimum of 40 seconds a mile faster than my current boat because that would afford us much greater range. I really wanted a boat that would sail to windward well, tack easily and is fast on a reach.
I had a real budget to maintain and for the size that I was looking for that restricted my choices to boats built in the mid- to early 1980''s.
I am not sure that I am actually answering your real question here. If not, I will watch for a clarification and see if I can be of more help.