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you can 1000% survive w/ RWD & snows. Chicago has zero hills and aside from the occasional 1-2 day snowmageddon the roads are clear.
If you're living downtown there will be no concerns. If you're living in a neighborhood where your garage access is via an alley you may have some occasional clearance issues but that's about it.
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"... if he fails, at least he fails while daring greatly, so that his place shall never be with those cold and timid souls who knew neither victory nor defeat.” —Theodore Roosevelt
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