Re: First Sailboat - the search
Welcome! What is it that made the Westerly attractive to you? What's your budget? How do you plan on using the boat? Is there more to your family than just your wife and you? With how many people will you be sailing regularly?
You mention 25-30's. You'll find here that, for a first boat, many encourage you to look at Catalinas. They are good starter boats for a variety of reasons, including that the company is still in business, they sold a TON of boats so there is a real aftermarket that manufactures all sorts of parts (replacement and upgrade) for the boats, and they can be found for reasonable prices. They also made them in a variety of configurations, including keel types, so you'll likely find one that meets your needs.
One of the biggest reasons I suggest a Catalina is that, in the used market, they tend to hold their value. That is, if you pay $10,000 for a Catalina 27, you'll likely be able to sell it in 2-3 years for about the same amount. Now, you may put $3-4,000 into the boat (adding roller furling, getting new sails, etc.), but at least you can kind of predict what she'll sell for and you can make intelligent decisions as to whether any particular upgrade is cost effective based on your plans for the boat.
In my very limited experience, I think you should expect your first boat to only be "yours" for a year or two. You're new, and (with al due respect) you likely have no real clue how you'll actually use the boat. After a year or two of use, you'll start to realize what the boat's shortcomings are, what you'd like to change, what you can live with, etc., and if you really love sailing and owning a boat, you'll probably be ready to switch to something else. This goes beyond just the "2-foot-itis" that we all deal with, it's a matter of finding a boat that actually meets your needs/wants. Thus, I would suggest finding a commodity boat and sailing the heck out of it for a year or two, then flipping it and finding something that might be your longer-term boat.
Of course, you may stumble across a 1990's-era, 32' Hinckley that's in beautiful condition and the owner "just wants to get rid of it" and will sell it to you for $5,000, in which case you should absolutely ignore my advice, assuming the boat meets most of your basic requirements!
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