I just purchased my first sailboat so I can relate. It took me 2 years to finally figure out what I was looking for then find the right boat at a good price. I ended up spending less than I thought!
One thing I can tell you is that what you think you want in a boat now, might not be what you end up with. There is almost always a trade off unless you have an unlimited budget. Look at as many boats as you can. You will learn more climbing ladders and walking docks than you think! Differences that you can''t see now will become common knowledge.
This is the short version of my story:
1) I learned to sail on a hunter. They are modern looking an roomy. I even considered the Hunter 26 trailersailer.
2)I figured O''days and Catalinas are a little stronger (maybe) and still roomy below with alot of extras for the $$$
3)I decided that I wanted a generaly stronger boat that might be a tad faster so I started looking at Tartans. But, there was not that many for sale in my area and price range.
4)I started looking at slightly smaller 27-28 Odays, Catalinas, and Newports. Still kind of cheaply made but a great bargain and lots of room below for what I needed.
5)I almost bought an older, but really nice Columbia 28. It was not what I wanted but the price was rock bottom (owner was moving and had to sell fast). I figured I could always sell it in a couple of years.
6)Started looking at C&C 29 - 31. My search ended there. (but a bigger Tarten is in the distant future lol).
I am far from an expert on any sailboat. I am just relating what I learned and how your views might change in time. Keep and open mind.
Good luck and get a survey!