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I was in the same situation recently, and it was a maddening few weeks of trying to think through it all.
I loved that the Monogram Series had the key JDM/Euro-market GT86 features (Leather, Dual A/C with nicer switches, keyless ignition/entry, upgraded headlights, frame-less mirror and so on...) -- and it was a great $ deal at the time -- but given the limited 2014 production/availability, only option now is to pick one up used.
I happened to come across two relatively-low mileage 2014 Monogram Series models at my local dealers in the low $20k range, however they were both slightly scratched up, had worn steering wheels and shifters, etc., and did not look like they were very exceptionally cared for. As go_a_way1 previously mentioned, if you're going to take exceptional care of your car and keep it for the long run, buying used versions like these will bother you.
I also started thinking about the slight model changes/improvements that have occurred since the 2014 Monogram Series was released, such as the shark fin antenna, slight cosmetic changes, reverse camera, upgraded head unit, fog light availability, better handling/suspension changes (I prefer current setup). Also, I personally prefer the rear end without the standard Monogram Series spoiler (could swap trunks, I know).
I considered all of the changes I'd need to make to the 2014 Monogram Series to get the newer improvements, as well as the changes I could make to the 2016 model, and in the end, I went with a 2016 model, as it would be easier and it's BRAND NEW. I've already ordered the upgraded headlights, frame-less mirror, and even the leather rear-seat armrest as a start. I'm willing to live with the nice standard seats, standard ignition, and standard A/C, in the end, in order to get a brand new, clean vehicle, with all improvements included right out of the box (buying used just to save $ was obviously not a consideration for me either).
That was my thought process... hope it helps, either way.
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