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Ramona said..
20 grand puts you in the 30 footer bracket these days. Not sure why anyone would have wheel steering and an anchor winch on a 27 footer. Nice interior.
20 grand will put you in a very old 30 footer that needs another 20 grand spent on it. No anchor winch is fine if you have only a small anchor and 2m of chain and anchor in 5m of water. If you want a good nights sleep you want a decent anchor and 10m of chain or better all chain. Try pulling that up by hand in 20m of water. I would not have a boat over 2 ton without an anchor winch. Wheel and tiller steering both have their pros and cons so that comes down to user preference.
For a first boat a Space Sailer 27 is an excellent boat. They are very roomy, sail well, one of the best 27' sea handling boats and very forgiving for a beginner. If the boat has a good motor and reasonable sails I think 18 grand would be a reasonable price which leaves you a couple of grand to replace the standing rigging.