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i had the exact same question as OP when i was in the market for a new car. i was on the fence about getting a CPO '08 328i coupe, or waiting for more '09s to come on the lot. in the end i ended up getting an '08 because the 'perfect' one came by.
i was afraid that i'd be 'missing out' on all the features of the '09 iDrive, but to be honest i'm perfectly fine with the '08 version. yeah it might not be as fancy looking, but it plays music off my iPod/iPhone, has bluetooth to make phone calls with easy buttons on the steering wheel to activate it, and it works. it took me maybe a few drives before i figured out all the common commands i could say as well as how many clicks to spin the wheel without looking, but it's perfectly fine to me.
if i had an '08 and '09 side by side and for close to the same price would i take the '09? of course, but there weren't any and i don't feel like i had to 'settle' for an '08. no regrets on my end.
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