Sorry everyone, this is going to be a little winded.
I bought an '07 base a few years ago with 95k on the clock. No maintenance records, no PPI. Looked over the car, found one door ding, no fluid leaks or funky noises. Drove great.
As preventive maintenance I did the water pump, lower temp thermostat, changed all the fluids, plugs and coil packs. Plus gave it a deep cleaning since the interior needed some attention. Removed the front bumper and cleaned the condenser coils and radiators. Plus it needed tires. Price was a steal, so I was willing to put some money and work into it.
Car has about 115k on it now and has been reliable. A few things have gone wrong as to be expected on an older car with some miles on it.
Typical starter failure (bendex gear sticking)
AOS Replacement
Evap test pump failure (that was a funky one)
Bad window regulator
Motor Mount
Alternator (not surprising since it gets poor air flow)
None of the issues are earth shattering and just wear items in my mind. I recently did a 3,200+ mile, 6 state road trip in the car and it performed flawlessly. Super comfortable and it just loves to be driven.
I do all of my own work and it's not a difficult car to work on. Access to things can be a bit tight at times, but patience and thinking through the process will serve you well. I went quite a while without having to do anything other than oil changes, then noticed some funky electrical issues popping up. Wrestled the alternator out (original to the car). When I saw the cooked windings on the back, gave it a sniff test, I knew it was toast. Tested bad, ordered a replacement from my local FLAPS.
Not at all worried about the IMS. Car still has the original shift cables and clutch. From what I've read the shift cables do not appear to be a problem on the 5 speed cars. The cable routing is different and doesn't put anywhere near the amount of strain on the ends as the 6 speed cars.
Installed a Soul cat-back exhaust and love the sound. Will get their long tube headers at some point. If the engine were to grenade, I'd find a low mile used engine and swap it in.
Anyway, that's my experience with a Cayman for what it's worth. Just a bit of insight from someone who bought one without a PPI and what I've come across so far. Good luck in your search!