I second Siamese's suggestion that you take your time.
I have been looking for over three years for the right boat, and I am still looking. I have posted about several of my rejects on this site. Look through my previous posts if you are interested.
What I will tell you is to figure out how much money that you can dedicate
to buying your boat. Then take 70% of that, and that will be your boat buying budget. The extra 30% will be for surveying the vessel, refitting the vessel to your specific standards, insurance, and hidden surprises. Stuff breaks when you least expect it to; be ready to shell out extra cash.
Here are a couple of things that I will pass along based on my learning experience;
- Rigging in salt water has a 15 year life span
- Sails, depending on use, have a similar lifespan
- engine & transmission - think of 1K hours as 25-30K miles on a car
- most decks, and some hulls were built as a sandwich with fiberglass on the outside, and either balsa wood, marine plywood, or special foam as the core. If the core is any kind of wood, and it gets wet, problems will arise. Look through the NUMEROUS threads on Sailnet to gain an understanding of this issue.
You will get to know brokers. Some of them are great, others are a pain in the neck, but you will have to deal with many of them. Realize that until you have bought a boat, that the broker works first for himself, second for the seller (who pays him a commission of 5-10%), and lastly for you.
If you are interested in a boat, call the broker and ask to see it. Do not worry too much about the price. You will probably make offers on several boats (I know that I have). When it comes to an offer, I try not to make an offer "insulting" to the seller. If the seller is asking X (say $100K), and I think that the boat is worth Y ($70K), and the difference between X and Y is greater than 20% (in this case it is) then I make no offer at all, and move on to the next boat. After a couple of months of no offers, the owners sometimes get the picture and lower their asking price. However, there are exceptions. I know of at least one Pearson 36-2 that has been on the market longer than I have.
Good boats sell quickly, and for top dollar. Boats that are well maintained are worth it, and you should jump on them quickly. One member came up with a list that he shares with his broker to find "the perfect boat." Here is a link to that list.
Unfortunately, every boat is it's owner's baby, and the owners love them. Therefore, most owners are blind to the actual condition of their boats with respect to other boats on the market, and they ask top dollar regardless of condition. In the owner's defense, they usually paid more than they are selling the boat for, and they have probably put a lot of money into maintaining them. However, the situation frequently arises where after you would purchase a given boat, you would have to put more money into a boat during the post sale cleanup and re-fit, than the boat is worth. I hate to be the guy to tell the broker, or the owner, that his baby is ugly, but sometimes it has to be done. Some brokers hate me, but I'm fine with that. Prepare yourself to become unpopular with some brokers.
...and perhaps the most important lesson of all: there will always be another boat.