I started on a Cornado 15 (#164) in the 70's. I know many folks who learned on 22 to 30 footers on their own and in sailing schools. A good route may be . . . buy the 27 and take classes on small boats. Maybe go for some ASA or US Sailing classes before you buy anything . . . to get the feel before you commit.
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"I cannot not sail" - E. B. White