With no sailing experience whatsoever, I bought a Grampian 23 last year that I had to move about 30 miles up the Chesapeake. Fortunately, I had a couple of avid sailor friends, and we got it all home in one piece. If it hadn't been for the friends, I wouldn't have known even how to raise the sails.
I have lots of experience on the water but none with sailing. Whereas in addition to steering the powerboat has four basic parts (forward, reverse, fast and slow) the sailboat has a squillion parts and you have to know where they all connect.
But, I'm learning. The SN forum is a great resource.