Oh man, I don't typically mentally order them at all, but I guess the top ones would be something like this :

For Girls Who Grow Plump in the Night
In the Land of Grey and Pink
If I could Do It All Over Again, I'd Do It All Over You
Caravan
Cunning Stunts
Blind Dog at St. Dunstans
Waterloo Lily

To be honest, I'm confused as to how to arrange the last three there and I guess I could do it different on a different day. I'll say that I don't mind so much the "west coast" ish sound Caravan adopted after Plump Girls.

Plump Girls was the last brilliant album by them in my opinion, but they still put out some nice songs here and there.

I agree with the order of your first three picks, but I was never much of a fan of the debut album, I always thought the singing let down the album. As for the other picks need to listen to them again.

I really, really need to listen to this band more. I only know In the Land of Grey and Pink right now. Reading through this thread I think I'm going to start with For Girls Who Grow Plump in the Night.

Let us know how that goes :)