As mentioned, this a hard call to make.
So, I give a little on how I doing and I not rush when I buy. I will know when it what I want and Price. Also, I have certain time frames (Time of year and weather) when I buy as I will move the boat by sea and not truck.
I down to 17 Sailboats in my watch list. This changes +/- as I find others or some are sold. I boat them in my favorites in a folder "Boats to Watch". I rename the link, here just a Example; Pearson 30' $10,000
It then have a record of price when I first find and if it go down. I check my links regular and remove if the boat is sold.
When I first started looking 2 years ago I wanted everything I seen.
I started doing research on the various boats and even read the "boat reviews" here and other places.
Then I narrowed down to the Rigging, did I want a Sloop or Yawl? Did I want a Cruiser or Cruiser/Racer etc.? Full Keel? I even measured inside my house to keep my focus of the space I would have. So, I know from Visual in the house how a 30' compare to a 38'.
I read about engines and Electronics and price stuff. For example; say a boat come with Radar? I can see this may have some bearing on paying a little more money over buying new later. So, basically I do math on what it have compared with what I want and will buy.
By taking time to look and read and see what people say here and there, after 2 years I went from wanting everything to 17 boats.
As far as personal preference everyone have those. But, we also can learn, we will love the boat we own.
So, Set a limit what you will pay, when you will buy. Get your mind on the Sail Plan you want. All these things so you narrow down your search. There no need waisting time looking at a Yawl, when you want a Sloop? Believe me, when you narrow down over time what you feel you want and know what you look for you can look more effectively and cull out the unwanted.
I hope to buy within the next 3 years as I gave myself 5 years to look and focus on what I really want. I see boats all the time that fall into my want list and price range. In two years I have found 2 Boats I really, really wanted and they sold before I could jump, so, I knew I had spotted a great boat! I will see more and in time I be the one that buy before the other guy.
One last word. My friends have supported me very well in this. When I first wanted everything they tell me, that not the Sail Rig you said you wanted or that too short for your minimum length (Some were too long), so wait!
I not sure I helped much and I sure not going to say what I look for and get beat to the punch again!