I'm 60 with all the same bills paid and kids off, blah, blah, ain't it great?
I have a gorgeous 2006S I need to sell because of business opportunity and I DESPISE debt.
It has 49k on the clock, had 11k when I bought it and it hasn't so much as hic-cupped in the time I've had it.
You can see it here -
http://www.premierautosource.com/boxster.php
Price is negotiable.
But to answer your questions I preferred the 987 (2005 and on) for several reasons - convenience, comfort, style and room were most important. The S is so damned fast, I would think I may have been as happy with a base model (who am I trying to kid??) There is also a huge difference in the operation of the power top
from the 986s I tested to my 987.
Watch ones loaded with options as they are not necessary to really, really enjoy the car and are also more crap to need fixed as well as adding weight to the car.
Try to carry a power adjustable seat acroos the garage.
One option I would not buy one without are either the Lightronics on 986 or ()even superior) BiZenon on 987. These lights are like having daylight for 1/4 mile in front of the car.
IMS is a factor, but just like the RX8 forum I used to belong to, owners with problems tend to take over the site and make problems seem far worse than they really are.