russo

CCW with the R888 is a good choice. I used to drive them to the track, approximately 60 miles round trip. I recently purchased a trailer to haul my 997 with an extra set of CCW (Custom Concept Wheels) with the 888's. By the way, if you drive to the track you will need to bring a spare tire just in case. On my last event one of my tires malfunctioned, broken valve, and thus was not able to continue. Replaced the flat with the spare, loaded up on the trailer and went home. The following Monday ordered a duplicate set of wheels so if the same occurrence happens I can to continue to have fun.

Verde

Agree with the comments re sticking with street tires until you're ready; and 18" wheels with PS Cups when you are. And lower pressure early in the day seems like common practice.
I would add that, in addition to bleeding the brakes, I'd replace the OEM brake lines with stainless ones. Low cost mod ($200 or so) and vastly improves pedal feel. I just putt putt on the street with my car and it's quite an improvement. The car should ship from the factory this way.
Oh, and don't forget to pack a good torque wrench. And use it on the lugs every time you're heading out for some more laps.
Apologies for not really addressing any of your questions

RonCT

Never found the need to swap Porsche brake lines and read somewhere they are a braided mesh core under the final black coating. Always had great feel and when I've asked my Porsche race prep shops about SS, they said "not necessary with Porsche - OEM are the way to go..." Never bothered to confirm exactly how the Porsche lines are made, but these guys know their Porsches.