Man that sucks about the bumper... sucks even more an old skool T-Bird had to take damage...
People with nice cars need to be more careful! Especially a '66 *anything*... think about how useless the tires and brakes on that car are in snow/ice/wet compared to a modern vehicle!
I think you've got the right idea about waiting for the spring before getting it fixed. I've got a list of about 5 dents I want removed, and a new windshield come spring. I figure, what's the point of fixing it all, then getting nailed by hail or something. When the sun comes out for spring so do the dent doctors...