Thanks all for the feedback, I wasn't expecting such a response, so really pleased to get all the different views and suggestions.
To answer some of the questions:-
I would be using the car as a daily driver, however I don't do daily miles, more very short trips or a bigger trip once or twice a month (+100 miles), so based on the mileage habit it will fall into a weekend car.
Based on some of the feedback and also based on general driving preference I'd be looking to favour the manual.
Tracking the car isn't a priority for me, but 'driving' the car is, probably the biggest draw to the Cayman for me are the continuous comments around it being a drivers car, I've owned a few of the other cars that have been put into this category (Civic Type-R EP3, VW Golf R, VW Golf GTI, Audi TT) so keen to experience a Cayman.
I'm still stuck between the Gen 1 S or the Gen 2 base, the budget is set but it puts me between a Gen 1 S with some money aside incase of any horrors or a Gen 2, albeit some would say the 'safer' option but it would be higher mileage. One thing i'm discovering with the Gen 2 base is they are wearing only the 18' alloys in most cases, I'm very keen to get the 19' alloys, which is a given on the Gen 1 S, I could always add at a later date but an original second hand set isn't cheap and its unlikely I'll be ain a position to do it. Colour I'm not fussed about, nor the audio/nav options.
Aside from testing all models, what are the things to look out for on the Gen 1 S's when looking to buy? I do want to keep my options open on these, I do feel there is just a little more risk of getting bitten.
@Windymiller thanks for the link, stunning car, however over the budget, even if I begged, borrowed and stole I'd still be a good few grand short, that one is a reach too far, shame. Thanks for the meet invite also.
Below are some links of a few cars I've be looking at just so you can see where I'm pitching my search.
I'll keep you posted on my progress, thanks again all for your comments, really helpful.