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Re: Lets choose SmackDaddy's new boat...
--At one point he was seriously considering catamarans for a variety of reasons, but on the other hand after reading Glenn Damato's book, and his difficulties clawing off a lee shore, Smack was against even a full keel for its limitations to weather.
--It seems like the more he races, the more he likes performance.
There are several affordable (older) multihull designs that have weatherly performance. An Iroquois 30 comes to mind. Loaded for cruising it will only be as quick as a comparable length monohull but will outperform if kept light. All the other advantages still apply - super shallow draft, level sailing so longer passages are less tiresome, more privacy for occupants, unsinkable (or easily made so). When anchoring or mooring off during a blow multis may pitch but never roll, making for more comfort aboard. There are more advantages but I'll stop here; Smack likely knows them well.
I have a 30' one off catamaran that was moored (and properly prepped)during hurricane Isabel. Free to swing at will nothing happened to her. Most boats that suffered were dockside. Having to use a dinghy all the time isn't as convenient but it becomes an accepable part of boating after a short while. And multis can usually accomodate a dinghy with ease.