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Honda Insight.
Either generation.
1st gen you can get easily 50mpg just by driving it. It is only a 2 passenger and would fit well within your budget.
2nd gen would be close to being out of your price range and would require a few mods to reach 50mpg BUT youd be getting a relatively new car 2009+ and it would cost about 7-9k.
You mentioned you don't want to spend more because of depreciation and other factors BUT the 2009-2010 Insights price is already so low that I bet in 5 years a well looked after 2009 insight will still fetch 5k+ Look at the 1st gens.
or a Honda Civic hybrid.
For what your looking for a hybrid or TDI would be all that would fit the bill. With current gas prices and the cost difference between diesel and petrol Id go with a gas hybrid.
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