No one can tell you what the perfect boat is going to be. In the end, the perfect boat is the one that works best for you on all levels. After all, owning a boat is not something that most people need, it is a non-essential purchase so more time tends to go into the research phase. It is also quite a bit of work to own a boat. If you simply cannot hush that voice in your head that says you must own a boat, well then it would be best to put your search parameters on paper. It goes without saying but I can imagine you already have some idea of what type of boat you want.
In my case, being 27 when I decided I needed to spend all my pennies on a sailboat, I started with price. I set the absolute maximum I could spend. (Side note- I definitely started with looks EVERY time I searched for boats, but knew I would have to set other search parameters). When setting that number, remember to have a separate dollar amount for what can be spent getting the boat up to snuff and operating, especially if looking into a boat that needs mechanical or fiberglass work.
I also knew I wanted a manageable cruiser big enough for overnights and cocktail cruises with friends; had to be fiberglass, diesel engine preferred, good stability characteristics and good sailing performance. Above all, I needed a boat with a classic looking profile and traditional details. Looking back on it, it is a little scary how obsessed I was with aesthetics.
I spent most of my time searching on yachtworld, Soundings Magazine, Boattrader , Boats.com but I actually found what I was looking for in one of the local free publications in the Northeast; in my case it was Points East Magazine but those magazines are usually in all coastal regions and are usually a great way to find a quality for sale by owner boat, or used boats in brokerage. Some other examples include Latitude38 (West Coast), SpinSheet (Chesapeake Bay region) and in the back pages of magazines such as Sail, Sailing and Cruising World. There are usually classified ads for boats in online sailing forums as well. Ah, and we cannot forget the gem that is Craigslist, if anything some of the posts are good for a laugh.
Once I had found some local boats that fit my parameters, I set about emailing and calling with questions and making appointments and going to see boats. Check out Looking at Used Fiberglass Sailboats.