[Perfectlap]

If you are TRULY a roadster guy... you will come back to a Boxster after your 997S lease is up. If you don't miss it that much then you made the right choice.

If you can afford either and already have significant seat time in a Boxster , I would say go for the 997S to get the total Porsche experience. You would be in rare company as far as car loving guys go.

Personally, I have driven all the Boxsters(except the 3.4), all the 996's (except for the GT's) and a standard 997. None really gave me the urge to dump my 986S until I drove a CaymanS...and that's coming from a die hard roadster-phile.
The point being that Sports Coupes have their own draws that pull you in.
I frankly didn't see a huge jump in peformance between my 986S and the 987S (3.2). I'm not sure I would pass up on the chance to try something new for a chance at something so similar to what you already know.

p.s.
What's a 2nd hand 997S 3 year lease going for in these recession-nearing days?
Please say no more than $750.
I can't believe they make you put a down payment on a lease, that's just a back door way of raising your monthly payment. Unless you use your car for work, leases are every financial advisers worst nightmare and buying new isn't much better. I wonder which would be more of a $$$ hit (leasing for 3 years vs buying), Boxsters aren't holding value as well as they used to. But that's true of all Porsches today, too much supply and the shrinking credit market is drying up the pool of buyers. Bust some balls at the dealership they need your biz more than you need them.