Join Date: Feb 2000
Location: Annapolis, Md
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"Looking for the wind" doesn't really have much info about a real budget. It does say that you have carpentry experience but it doesn't say that that you have fiberglass, marine electrical, or any kind of boat repair experience.
There are a lot of beat to death old boats in south west Florida. Boats that have been baked in the sun until all sealants give up the ghost, and then rotted by the high humidity and heat.
In the 1960's through the 1980's there were a huge number of boats built in Largo, St. Pete and Clearwater. Many of these were comparatively inexpensive when new and are really cheap to buy today. But they are not free and fixing one up to a beater into a condition that will make even coastal sailing safe and possible is no small undertaking.
For example, you can find beat to death 1960's era Morgan 34's (nice boats for that area) for something like $15-20K and if you plan to put one in good sailing shape for perhaps $10-15K. Or an old 1970's Morgan Out Island 30 or 33 which are room boats for their length that make a reasonably good liveaboard but not especially well built or are good sailing boat for something under $20K. Another good option is the 1960's Irwin 32 or early 1970's Irwin 30's, which are available for something less than $15K. A great choice but one that is a little more expensive in the mid- $20K is the Pearson 323.
Anyway, at the heart of it, boats like any kind of home don't come free. You need to do some soul-searching and a sit down and figure out what you can afford, factor in the cost of dockage, and yard bills, living and housing costs while you are fixing up your future home.
Lastly, since your skillset includes carpentry, you might consider building something like Jay Benford's badger design using simple lumber yard materials, or one of Phil Bolgers simple designs.