A few things to think about
From your post, I concluded you're planning to keep the boat in the water. That's good...it's the best way to maximize your sailing time. However, depending on boat length and marina location and amenities, a slip may run $150 to $300 a month. Less expensive slips are usually farther away from open water (more motoring).You'll also need antifouling paint to protect the hull against barnacles, weeds and other sea life. Antifouling needs to be renewed every 12 to 24 months and can easily run over $1000 by the time you add the cost of hauling the boat, hull cleaning and prep and labor. To delay this expense try to find a boat with fresh bottom paint.If you trailer the boat, you won't have these costs, especially if you can keep the trailer in your yard or nearby. Maintenance will be simple because the boat will be close to home. However you'll need a tow vehicle and you'll have to rig and derig the boat every time you go sailing. That can add two hours of work to your sailing day, unless you can find a marina or yard that will let you store the boat on the trailer with the boat rigged.Considering these things will help you make some decisions. Some boats will be eliminated from your search as a result. That's OK, because your search will be more focused.As far as an actual starter boat, I think small boats are better for learning. They're responsive and offer more feedback to input than larger boats, so you will develop skills quickly. They are inexpensive to purchase and maintain (most costs are proportional to the square or cube of the length). If you find out that sailing isn't your thing, you won't lose as much when you sell the boat (you may even MAKE money!). That being said, it goes without saying that you should not buy a new boat.Here are a few suggestions (in no particular order) based on availability, cost, ease of sailing, room/comfort and stability:Keelboats:Catalina 25, Catalina 22, Hunter 23.5, Hunter 23, Hunter 19, Capri 24, Com-Pac 19, AquariusDaysailers:Flying Scot, Rhodes 19, Com-Pac 16, Precision 16, Capri 16Try to find a boat with decent sails and see if you can get someone with some experience to go shopping with you. Good luck and happy sailing.PeterH23 "Raven"