I'm probably going to be ignored for this, but I would recommend a PT Cruiser or an HHR (although I have never driven one). My PT gets constantly 500km/$60tank of gas (on empty), I can haul five people around when needed, I can take the rear seats out, and I have just as much room as my [first] Ranger did when it had the cap on. Parts are cheap as hell for them, and unless you're doing a timing belt or water pump, they aren't that bad to work on, they jut look bad. For a DD, I'd go with a small little car that meets the majority of your needs. The PT fit mine and aside from how the thing looks (at least its black and chrome with blacked out windows), I don't regret getting it, one bit. I picked mine up for $5500 with 150 000km on and it was all highway mileage.
Then to solve your problem for a tow rig, keep your eye out for an old beat up former work truck, doesn't have to look nice just as long as it can haul. An old Chevy from the early-mid 90's with the 350ci, bulletproof, and they're going for the $5000 and under mark here, with the 200000-250000km range. Get the gas pig and only use it when needed, and balm around in the city car the rest of the time.