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For maintenance/upkeep, we generally budget about 10% of the purchase price per year. Sometimes we go over this, like when we decide to awlgrip the hull. Other times we're under, and just buy a lot of soap and scrub brushes. Another boat you might want to consider is a C&C 27 or 28. They look good without having to be "shiny-bright-spiffed-up", and sail pretty nicely. They shouldn't be too deep for the shallow water around you. The Sabre 28 is also a nice boat, but IMHO needs to be kept to a higher degree of polish to look good than the C&C, and might not perform as well on those hot summer days with light and spotty wind. If you can get a copy of Practical Sailor's Buyer's Guide to Used Sailboats, (see their website or check the local library) it should give you a lot of interesting, informative and useful information.