Re: Sailing the Sydney to Hobart
I think the greatest resource for the information you seek is in the bar at your own club! My brother in law is a member there, and has done more than 30 Sydney-Hobarts. Guys like him could tell you exactly what to expect and how to prepare.
In general I would think you need to prove yourself to prospective skippers by doing smaller offshore races with them before they would consider you a candidate for the big race!
1979 Santana 30 Tall Rig