Re: Need help and advice on choosing a sailboat.
Welcome to Sailnet. Unless you have significant undisclosed experience, you'd probably be better served buying a small, higher performing boat while you developed boat handling and sail trim skills. If you have a smaller boats you will probably to sail it more frequently. Further smaller boats give immediate feedback that you wouldn't get on a bigger boat. Ask yourself, "Would I rather learn to drive with a Mini-Cooper or a Greyhound bus?"
Perhaps you can find a local venue with one-design racing. If so, you'll likely find a built community committed to support you while you develop. Additionally, the market value of most one-design boats is well established, which will make it easy to sell your boat when you want to move up.
While you're developing skills you should seek opportunities to sail on other people's boats. An easy way to achieve this is crewing on races. There are good posts up on how to get invited to crew, and the expectations of beginning crew.
Also during this period you can explore chartering to taste sailing on big boats and cruising.