Be a man. If you want a Porsche then get a 911
This statement is inevitably made by people who drive Honda Accords or 5 year old Chevy Silverados.
That new Boxster will rip off sub 5 second 0-60 runs and will give a Carrera a run for its money around a track. The ideal track car is the Cayman, but OP wants the wind in his hair. You can't go wrong with either, Porsche reliability is second to none. You will get nailed on resale buying new, but if no one bought new there wouldn't be good deals on CPO cars.
Eta: what sports convertible in the comparable range?
Thats the thing: There really isn't much else out there. The Jag XK? Terrible reliability. The Mercedes SL? Way softer. The BMW 650? A huge cruiser. Maybe a CPO Aston Martin Vantage (2007's go for about $70k), but where do you get it serviced in Louisiana? A Camaro ZL-1 is faster and cheaper, but then you'd have a Camaro.
This post was edited on 2/2 at 10:52 am