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I also have a high mileage X5 in VA and have contemplated with selling it for something else many times. If you're upside down, trading the car in is just plain dumb. If you're willing to eat the amount you're upside down and tack on another $20k+ loan, then that's all you. Financially speaking - you're much better off keeping the X5 and doing maintenance as necessary.
Jumping ship to another vehicle will eventually put you in the same boat again. Let's be honest, the X5 is still a ridiculously nice mode of transportation. If you feel the need to 'upgrade', do some tasteful mods -- perform a full detail job. It can quickly rekindle the BMW experience.
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