I've done 2 Porsche DE, and 2 club events, so 6 track days. I too started at novice and moved quickly up. Check your local PCA DE rules, they will list the colors. Here is a link the PCA in the SF Bay Area, with a good description of DE's. PCA GGR: Time Trialing with GGR


Smounic raises a good point about being comfortable in your group. Our PCA is incredibly safety conscious, and I've not yet seen any car-to-car contact. But its a very personal decision.

I prefer to be on the slower end of a faster run group: otherwise you get held up by the slower drivers, and spend more time in the congo line than on open track.

I don't think you need an instructor with a Cayman or Boxster for the first couple of events. In these you'll still be working on the basics, like driving the line, adjusting your braking zones, etc. and any instructor can help on these points. None of my instructors had Caymans, and all of them provided valuable insight and instruction.