Self insuring... a continuation of "an observation" (long)

[Perfectlap]

it sounds like you are planning to buy the car outright without any financing.
I really don't care to ever do that. So my plan was to buy a second hander with less than 15,000 miles. I was very successful (actually only took a week) and found my 2000 S with only 10,000 miles (its litterally brand new). I'm shooting to pay it off in 3 years with an extended service contract payment schedule for that period of time.
My advice would be to find the Boxster of your dreams with the lowest amount of miles that was garage kept with newest model year possible. Once you have wittled down how much of a budget you will propose for this, the next step will be to consider your safety net of extended warranty or going it solo.

I was long searching for a vintage 911 and a friend gave me some advice that seems to be the standard for Porsche buying:
Buy the newest Porsche you can afford.