[racer]

PPI should cover an oil change at your expense so you can have the oil filter removed and checked for Metal content. Early Caymans share IMS issues with all the 986/996 cars (boxster, cayman, 911) until the 987/997.2 cars came out and fixed it.

After that, check the boards here to see what issues are mentioned. Not sure of an actual buyers guide though. Looking local? follow JFP and Mike's comments. Gets a little harder when shopping out of your local area.

Also consider your own knowledge on the cars (or cars in general) to know what limits you are working with. You don't mention budget, but mentioned limited to a .1 car. Well, to me that means a higher miles car that might need things like Rubber bushings replaced. New Shocks? Motor mounts? Clutch if a manual? Tiptronic service? Check function of all factory options. Be sure to check any aftermarket items (like radios for instance)...

I imagine the old rule of thumb of maintain 10-15% of purchase price on hand to fix any issues that come up during the first year.

I go back and forth about a 986/987.1 car... and then figure I will wait another year (or 2 or 3) for a albeit higher mileage 987.2 car instead.