So, Honda really wants to buy my '07 Fit Sport back, since the resale market is so good and I've only got 90k on it I had been thinking '15 Outback, but now I'm considering a '15 Fit EX-L
I'm not sure how the hell I'd even buy one in Missouri. Plus it is fucking expensive. I can get a fully loaded Fit for $20k, Outback is about $30k, model S is $60k+. I adore my '07 Fit Sport, and the only thing it is missing is bluetooth connectivity and some more upscale interior, which I'd get with the '15, plus some kickass MPGs
Really it's up to what you can afford and what you enjoy driving. Take all the cars you're interested in out on a test drive, compare pros and cons of each, etc. I mean, if you enjoy the new Fit and can live without whatever extra you'd get from the Outback for $10-40k more, then go for the Fit.
If I made the move to Seattle, I'd be more tempted by the AWD of the Outback. As is, I don't really need the extra space, I just need a high mpg Dihm-mover that can fit a bunch of random shit in it now and then, and is moderately enjoyable to drive. The thing that makes me sad about the '15 Fit is they got rid of the "Sport" models. Steering is a bit more squishy, doesn't have the nicer rear axle, blah blah The HR-V seems interesting