my current thought is perhaps the "vintage" o'day daysailer. good starter? the recommended Lido, Capri or Lazer are great recommendations, but currently with my shopping in the southeastern section of USA , so far, out of my under $2k range. I'm configuring to shop...but at current, may go with the daysailer.
A daysailer would be a good bet. It's sufficiently forgiving that you won't go for any surprise swims. It's also built well enough you won't be likely to break it, and when you're ready to move on, it's a known quantity that you'll be able to sell. It's also small enough to sail by yourself, but big enough to take other people out too, so you don't HAVE to be alone if you don't want to be. If there's one nearby at the right price, a bird in hand is worth two out in the bush.