You can do a search on one of many boat selling websites for sailboats in that price range - and there will be many. But if you read enough ads you will start to learn the market. You can readily post an ad here if you find something interesting and you will get an earful. For what you are describing I would think you should look at the regular names, Pearson, O-Day, Catalina, Beneteau, Hunter, S2 (Just look at what boats are featured on forums - they mostly have stood the test of time and are successful designs).
As for your question about buying the last boat first, I think most of us would tell you it's best to learn on a small responsive boat. But lot's do it the other way and it can work fine.
Don't buy a pig sailboat - it's just a bad powerboat.
