1. Crew for someone else first to see how you like cats and racing cats compared to half-cats.
2. Decide on if your sailing will be mostly solo or with crew. It makes a BIG difference. You'll need to find someone who is as dedicated and available to the sport as you if you go that route. Sometimes a smaller single-hand boat can be easier because you don't have to rely on anyone else but yourself. <16' is typically solo, >18' is almost always with crew.
3. If you want to race, research local fleets. You'll want a type of boat so that you can do mostly one-design racing and not open class. It's so much nicer with "he/she across the line first wins" as compared to tracking time and adjusting based on ratings and what is the handicap, etc.
4. Based on #2, if you want to go the solo route - used or new Hobie Wave.
5. Based on #3, the lowest-cost route is a used Hobie-16 (2-person). If you're willing to spend more, than seriously consider the nearby fleets and what they race with.
6. If you're concerned about a strong boat that will last and can handle beaching, grounding and getting hit by other boats, dock, etc. - Hobie Wave or other rotomolded-hull boat. Nowhere near as fast as a Formula, Nacra, Inter, Hobie Tiger/Fox, etc. But those lightweight fiberglass boats can't be dragged over rocky beaches like a rotomolded plastic boat (same durable stuff as Little Tykes kiddie swingsets).
7. Remember that your first choice doesn't have to be your final choice. Many of us... most of us... all started out with cheap, used, Hobie 16's in the beginning. You can recover half or more of your $1,000 investment a few years later when you sell it and buy something else.

Yeah, for someone who doesn't sail one, I do sound partial to the Wave. For me, the appeal of solo, one-design racing with lots of competition in big fleets with a simple, easy to rig/haul/sail boat would be attractive. They may not go as fast, but when the fleet is all equal in equipment - it's all relative.