I started riding on the road in 2nd grade, along the Tamiami Trail in Florida. Then it was the main road down the Gulf Coast. It taught me to ride straight and to stay on the right of the white line.
The next big influence on my riding was Los Angeles. As a college student, riding 10-30 miles a day and influenced by California Traffic laws and Bicycling Magazine, I started using left turn lanes and positioning my bike according to the laws of California.
All of Florida was flat, and most of LA. But the Baldwin Hills, Palos Verdes Peninsula, and the Hollywood Hills taught me how to ride them. Back then I was very competitive. If I saw a bicycle ahead, the hunt/kill switch flipped and I would pursue them and overtake them. The foolishness of youth.
I've lived all around Southern California, from Santa Barbara, LA, San Diego and Palm Springs. San Diego was the most challenging because of its canyon and mesa topography.
But now I'm in Little Rock, AR. It's the toughest yet. Not many major hills, but if I ride 8 miles into downtown, its a roller coaster of 60' hills all the way in. The roads are narrow and potholed. There are only 3 roads in. One is a path along the river but wanders so it's longer, one goes straight in but is the worst road, and a third goes in from the south through some sketchier neighborhoods, but with a better road surface.
Most of my riding is commuting, shopping or getting to town for events. I tend to ride conservatively. Mostly a non-vc style developed in my youth on the Tamiami Trail. But its been successful. I ride to enjoy the view and my thoughts more than I ride to race.