Should I sell my '08 Sahara Unlimited and get a Crosstrek?

Knee-jerk reaction: Noooo!

Rationale: started freelancing photo/video, have to drive more often and further than previously. Jeep is a 2008 with ~83k on it, in pretty good shape. Came with roof rack, lights, lift and I've done nothing more to it. Has unresolved death-wobble. No leaks. Probably needs new shocks at some point, maybe springs, track-bar, other minor upgrades totaling ~$1500 over the next year or so. Interior is very good. KBB says I should be able to get $17-18k for it. Might be able to get a bit more with upgrades.

Subaru is a good company and I like their stuff. Used '16 Crosstrek is $20k and gets significantly better mileage. Still has 9" of clearance. But it's not a badass looking Jeep. I've spent less than $4k on maintenance and parts in the last six years, but I wonder if those days are coming to an end. Really hate to let the Jeep go, but maybe it's the wise decision.