I'm a huge fan of the World Sailing Offshore Special Regulations, and have always used them and their predecessors as a checklist when preparing a cruising boat to go offshore.
That said, when using this resource, it's as well to remember that these regulations were primarily written by people thinking about fully-crewed racing boats—yes, that's changing with the rise of double and singlehanded racing, but slowly.
A good example of where we in the shorthanded cruising community need to think differently from the Special Regulations is person overboard prevention and, more specifically, getting rid of sidedeck jacklines. But I have already written extensively on that.
There is also an area where I think the Special Regulations are plain wrong: