OK I think the picture helps me understand the Wild Cat thing:

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A wildcatter is a person who drills wildcat wells, which are oil wells drilled in areas not known to be oil fields

So a Wild Cat sailor sails wild cats around oil rigs, which are drilled mainly on the West Coast and in the Gulf not known to be sailing areas or do I still have it wrong?

Nice looking boat but no oil rigs in Florida. If Hobie would change the name to "CondoKat" it may take off down here ;-}