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This is a great post. I'm in the same boat and looking for a similar vehilce. While I do agree that the RAv4/CRV and Outback are all great choices, they don't meet the less than $5,000 that the OP listed as a maximum price range.
Wrong.
I purchased my 99 outback with 115k in October of last year for $4700.
It's in great shape and runs like a top. Getting an average of 26mpg is a nice plus too.
Gas mileage was a big reason I sold my 02 tahoe and bought this. 12mpg in a 7 passenger tahoe was too much when it was just me and my dog %95 of the time.
Rav4 and CRV's can be had in that price range also, but I've had experience with both and i'm not a huge fan.
If it came between those two, i'd choose a 1st gen crv. The b20 engine is reliable and easy to work on.