Derek,
I have a similar problem in that I would ONLY buy a 'demo' or very low mileage MINI again , deprecation was never a major problem in the early days of MINI . it looks an amazing looking MINI though , I am still struggling with the decision I may have to make , can I move back to a hatch from the Countryman
I did 600 km in a really good R56 S over the last few days to see if that would break the mental 'deadlock' and am still no clearer in My mind , I really love the CMS and had hoped the Clubman might do it for Us but I just can't warm to it --and that's leaving out the crazy pricing !!!! . I feel you need to go with your heart on this though , but I would recommend getting a demo JCW for a few days and do your normal driving stuff and at least that will answer some question I know are knocking around your head .
G