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As to the insurance, consider the typical buyer of a Boxster versus the 300Z. I have had 2 300Zs totaled within 100 feet of my former house. The good news is they protected their occupants. The typical Boxster owner is (my impression) more mature and insurance rates do vary by the age of the driver.
My 2 Boxsters have averaged less than $20 a month is unscheduled maintenance. I drive mine 9 plus months a year. It isn't my only car. I have an '01. I have driven it regularly to work. Just took it and my wife 55 miles and back yesterday through hard rainshowers.