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If your now leaning towards sub 3k and want to put alot of miles on it (leased cars) I think a 01 jetta TDI would be the only candidate. Obviously looks are important to you the newer body style jettas dont look dated.
a 1st gen insight can be had for around that if its a bit rough. Would lose absolutely 0 value driving it. Same goes for the jetta.
Besides that your looking at late model civics and the type. Not as nice looking but much more reliable.
I still think based on what youve said a 2nd Gen honda insight makes the most sense. It may cost 7-8k but you will get great gas mileage it fits 4 adults easy looks like a pretty normal sedan and Its depreciation in the next few years I think can easily be offset by dramatically lower repair bills.
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