...To be told to spend twice the money to be able to race a boat that isn't going to be competitive isn't going to happen.
I'd like to do some sailboat racing. Maybe a few times a year. I'm not looking to invest five thousand or more to get a competitive boat. I'm just looking for a little bit of fun. Choice is to take my older Hobie, that I know isn't as fast as a modern boat, and drive a few hours, and be told that maybe I can race, but I'll be illegal, or maybe I can't race, doesn't seem like a good use of my time.
Instead, maybe I should pick up a used Sunfish or Laser, both of which are a hell of a lot more active in my area, and race that and save the Hobie for when I'm by myself. Less then a thousand bucks and I'll be somewhat competitive...
It's not clear to me if you want to be competitive or not. You won't be with your Hobie, no matter what, but you expect to be with the other boats. You're comparing apples and oranges. If you do want to be competitive, the H16 is out because you have excluded your two options (newer boat and HCA-legal equipment on existing boat).
If I were in your position and wanted to race, I'd start off by seeing what sort of racing as happening in my area and then plan my equipment around that. HCA-only? Go for the Sunfish or Laser. Cat racing that isn't strictly HCA? Sail what you have. But if you prefer sailing your cat, spending $1000 on a noncompetitive Sunfish or Laser doesn't seem better than spending the same on improving your existing H16 and making it legal.
Have you talked to your 'local' race organizers?
'00 H16 #104691 - '78 H16 #32692 ex-rental - Old Holsclaw trailerMy Hobie 16 pages