Well, there are a couple of ways to look at it. First, how much does it cost to operate your boat annually? Then how many more months would you be at sea by rounding the horn? Do the math, including the extra wear and tear that goes with equipping a boat and sailing in high latitude environments, and that $1000 looks very reasonable if not downright dirt cheap. Go around the Horn because you desire to, certainly NOT to save money.
A Hunter or Catalina around the Horn? With the right weather window, sure. You might have to wait a hell of a long while to get it though
Speaking only for myself, I'd prefer a tougher boat than the Hunters or Catalinas. Structural damage to a hull in prolonged heavy weather? Depends on the boat (age, construction, etc...), but hulls are incredibly tough. Contact with solid objects; containers, whales, and the like are probably the larger causes of significant structural damage. Then there's the more likely scenario is getting rolled by a large wave and loosing your rig
A couple of books I mentioned before ( I think it was to you) that will give you a better idea of basic design and voyaging issues are:
Yacht Design According to Perry by Robert H. Perry
The Voyager's Handbook: The Essential Guide to Blue Water Cruising
Adlard Coles' Heavy Weather Sailing
They're nice books to help you develop a baseline of ideas, and then hopefully refine them with your own experiences.
Read, read, read, everything about boats and voyaging that you can, and sail sail sail on other people's boats until you have enough of an experiential baseline to decide what kind of boat you 'need', and work work work to save $$$ for your voyage.