I bought a Cayman R in February after spending most of lockdown researching what to buy. Initially was looking at a gen.1 Cayman S as they are cheap, but realised that spending the extra 10K on a gen.2 would be the right thing to do, eliminating any possible IMS or bore scoring issues and having a much better engine and slightly improved interior.
I then popped into Porsche Stockport to test drive a high spec 981 Boxster (as a second car I really wanted a droptop, but every time I've gone to buy one I end up with a coupe) and while there they had a Gen.2 Cayman 2.9 in mint condition. Drove both, loved the looks and interior of the more modern 981, however the gen.2 987 just felt like a much more engaging car to drive and I actually preferred the more old school interior (that central console in post 981/991/992/718 Porsches looks great, but I feel it gets in the way and the buttons are a distraction) I'm not a car driving expert, but I guess the analogue feel of the gen.2 987 came through, but you still have the newer DFI engine that's in the 981.
So fast forward a few months of looking on Auto Trader and Friends Green Porsche. Started to consider a 996 4S as I think they have become a real classic, or possibly a 997.1 but then a Cayman R comes up on FGP website at an affordable price, 15K less than all other Cayman R's. Why, because it had 98k miles, no bucket seats and PDK. However it was in Platinum Silver which looks stunning and had had an absolutely impeccable service history, with the previous owner having just replaced all the suspension with Öhlins Road & Track suspension, GT3 master brake cylinder and braided hoses. I could afford this, Porsche buyers get so hung up on milage, but modern cars last for ever if well maintained and Porsches even more so. If I had bought a Gen.2 Cayman S I would have wanted to change the alloys, lower the suspension, tweak the ECU, tweak the breaks. All these things are already done on the R, plus it has the extra downforce and the slip diff. It was a no brainer and I absolutely love this car, honestly I don't see what I could replace it with for £30k. Not even an R8 which I did consider. I was tempted by a 996 4S but the Cayman R is a modern car I can use every day, where as the 996 is pushing 20 years old. It's unbelievably fast and the handling is sublime. Yes a manual would be better but I'm pushing 50 and probably will keep this car 10 years, so the PDK suits me and is excellent for those long road trips that last the whole day. It gets noticed too, popped to Caffeine & Machine and it's great to have people taking photos of your car. Yes a GT4 maybe better and my dream car would be a 981 Spyder, but these are both now over £75k same with a 991 Targa. All the other R's are in the £40k mark too. So I probably have the highest milage Cayman R in the country, but it fits my budget and I feel very lucky.
And on a side note, my friend bought an immaculate 997.1 S for the same money, had a bore score check, had immaculate service history. Spent £4k on it straight away he had done only 600 miles in it over a few months. I met up with him in my R and he started to get white smoke out of the left exhaust (so problem with the right cylinders) loss off coolant. Yep major engine rebuild for £14k. So he would have been better spending an extra £10k for a gen.2 with the DFI engine. Really felt for him, it's still getting repaired 6 weeks on.
I also feel that the 987's will become a true classic over time. Like the 996 everyone hated it at first. The original Cayman was always joked at as the poor man's 911 or a girls car, which is a joke really. It's a mid engined, 2 seater, light weight Porsche. It's as if you have all the attributes of a Lotus but with a flat 6 and German engineering FFS. The curves are stunning, the lights still have that original frog light look, which went with the 981. You have a naturally aspirated 3.4 DFI engine, analogue steering, stunning curves and with the R a very rare car.