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With that kind of budget, and looking for a trailer sailer, you have a lot of choices. However if you want to tow it home after every sail your choices get limited real quick unless you don't mind a lot of work. The larger the boat the longer it takes to rig. That said my favorite trailerables that will still be reasonable to rig, have plenty of room for 2 to overnight, and have a decent turn of speed. Catalina 22 (sport or MKII), Precision 23, both can be bought new in your budget. The Precision would be right up at the limit, but you could always buy a few years old. They are a bit better built than the Catalina IMHO.
Catalina 22 Sports start at $15,000 or so new
Catalina 22 MKII (the one you want for racing other C22's) starts in the low $20,000 range
Precision 23 is much more, like mid $30,000 range, but it's a lot of boat.
These boats are quite large to trailer, and step the mast as I said. A small daysiler/cruiser is much easier (Catalina 18, Precision 18) but they are really cramped. I have (had, just sold) an O'day 19. It is not a boat I would want to rig every sail, or overnight in. I kept it in a slip and just daysailed it. In hindsight I would rather have had a 22' to 23' boat as my first small cruiser, the 192 was useless as a cruiser and an average daysailer at best, it's a compromise.
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Technician, RCR Yachts Buffalo.