Big man/Small Car. How do I into bigger car?

So, after last week's adventure at the Chevy dealership, my wife and I have decided that the Mini has to go. It's too small, harsh riding (she had a back injury last year, and mine's no worse for the wear) and impractical for stuff we'd like to be doing (eg. kayaking, building stuff). After we hit a big enough crack in the road to send both our backs into a raging fury, we agreed that if I could lower my car payment by $100/mo to about $315/mo, that I have license to get anything I want if it means getting out of said English car.

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I worked in the car business long enough to know that I am not going to get nearly what I owe on my Mini on a trade, so I went ahead and put it on Craigslist in hopes that I'll find someone who has that kind of cheddar to spend. Failing that, I am prepared to roll at least $3k of negative equity into a used vehicle costing roughly $13k to get that payment into that range. Has my optimism really been that dashed by that lowball trade figure from Chevy? What do you all think?

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