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It's never a smart decision to get upside-down on a car, and to bring even more upside-down-ness from your last car to stack on top of (under?) the upside-down-ness of a new car is never ever going to make financial sense.
That said, I don't know if choosing an FR-S is an entirely logical and practical choice. I mean, it's not the least expensive transport out there and it's certainly not the most practical.
Even considering that, there can't be a worse time for you to buy this car than right now. I would wait at least until the trade-in is no longer under water before shopping. I also can't say I wouldn't understand if you ignored me entirely.
-Justin
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