OP, correct me if I'm wrong, but in the last 4 years you've gone from F150 to Escape to F150 to Expedition to C-Max? I can't imagine you're saving much money overall by changing vehicles this often.
I will however second that I vastly prefer driving my 1850lb Insight to either my work van or F150 (which my father mostly uses) in Vermont winters. Heavy, rear wheel drive vehicles with high centers of gravity have a much greater tendency to slide, and are more likely to tip - ask me how I know.
Plus, I have no issues towing with my little 67HP, 70+ MPG FWD car. I've nearly matched redpoint5's 1800lb figure. Although larger vehicles can (generally) safely tow more, you can theoretically tow anything with anything, and I've logged thousands of miles pulling over 1000lbs behind my car.
Not that I'm advising you go out and buy an Insight, just suggesting you may not need as much vehicle as you think you do.