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Please read my last post on the "Build a Trailer" thread.
You are probably over thinking the situation. The first boat you get is not likely to be your last one if you stick with sailing. In the beginning, you are not going to cross the gulf, or sail around the world. Those ambitions are for later after you get some experience. Just find a boat in your price range that is in good condition, buy it and see how it works out. Most any brand will be fine. Later as you gain experience, you'll learn what is important to you, and the next boat a few years down the road can be tailored to your sailing objectives. Avoid the temptation to buy larger at the expense of good condition...you don't want to have something that is always broken and requires constant effort and money to repair or restore (sometimes called upgrades by the people doing it.)
And before you buy, visit the book store and buy/read some basic books on sailing...leave the bluewater, around the world ones until later. You need to get the basics mastered first. Advanced sailing can follow later.
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