I would start wi the club's locally. There are a number of boats that could work, but sailing something that has a local presence would be my first priority. If you want to branch out on your own I would recommend you to take a look at one of the RS (RS is the name of a manufacturer btw) line of boats. They will be at the top end of your budget
, since you will be pretty locked into a newish boat but are worlds better sailers than a lot of older options. Option 2 would be a used Weta, these are small trimarans, so are far less likely to flip, they typically race
with one, but sail with two.
On the inexpensive side you could look at a V-15, or similar two person dinghy
. In this price
range the trailer will cost as much as the boat, so there isn't much risk. A good version runs about $3k.
But I really think sailing whatever is sailed locally is the best option. At least until you understand why that boat is so popular in local waters. It also makes flipping the boat quick and easy if you decide to sell it, because there is an established market locally.