Well, aiming for a purchase next Spring, if I were you, I would start watching the Houston Craigslist boat section:
houston boats classifieds - craigslist
often, starting in the Fall. I don't want to over generalize, but one problem with Craigslist is that you often have to make snap decisions to get the better deals. In the Fall and Winter, boats tend to sell slower and it can give you more time to look into it before jumping on it. But even if it doesn't, I know I learn better researching a real potential purchase than a theoretical one. Maybe you see a Daysailer at a given price and you look into whether it would work for you, what's included and whether it's a good value. You decide it is and reply only to find out it's gone. But then the next time one shows up, you can probably decide quickly if it is worth pursuing. An because you started in the Fall, you have time for "next times" and you can wait for the better deals.