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Do you have equity in your current car? If you're upside down, I'd just keep what you have and not worry about it.
As far as maintenance, change the fluid every 30K miles and change the clutch when it starts to fail.
Things to watch out for: downshifting too far. Going from 5th to 2nd instead of 4th and then letting the clutch out is a great way to get a mechanical over-rev and possibly blow your engine. Otherwise, as a first time manual, you'll put additional wear on your clutch until you figure things out. Not a big deal.
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