It's hard for me to answer your poll. I think of "hilly" in terms of locale, not by how much actual climbing. Rides in and around Indianapolis, where I live, are all flat and are listed as such on my Bikejournal entries. There may be a minor hill or two, but you REALLY have to go out of your way to find them.
If I head about 30 to 40 miles south of Indy, it's what I consider to be hilly--of the short and steep variety. I list most of those rides as "hilly" although the total altitude gain is still pretty low.
If I head even farther south--to Kentucky or Tennessee--then I can really hit some hills, but it's rare that I get to climb an actual "mountain." I think the longest sustained climb I've done is about 3 miles.
I'd really like to climb more.
Because I don't climb much, I'm liable to view any ride that has at least 4 or 5good climbs as "hilly."
Live with intention. Walk to the edge. Listen hard. Practice wellness. Play with abandon. Laugh. Choose with no regret. Continue to learn. Appreciate your friends. Do what you love. Live as if this is all there is.
--Mary Anne Radmacher