There are plenty of good, sailable trailer boats available for less than $2000. Look on sailboatlistings.com and searchtempest.com.
My opinion is that trailer sloops (one of my requirements) are all quite similar within two categories: some are more sporty, meaning more complex rigging
and planing hulls; others are more more family-oriented, simpler rigs, and more stable. My thinking was to choose which category (the latter for me), define my price
range (<$2000), and then find a boat that I could sail the very day I bought it. NO PROJECT
BOAT! I ended up with an O'Day Mariner just by chance of what was available when I was shopping
. I'm satisfied with it and I think that I would feel the same with most, if not all, the sailboats that fit my criteria. In other words, don't get hung up on a particular maker or model.
In small boats, age doesn't matter as much as condition. A good owners' association is worth a lot and is usually indicative of a popular and plentiful boat model that has held up over the years.