According to my wife, it's not dessert unless it's chocolate. I don't go quite that far, but if offered fruit for dessert I would wonder where the crust & sauce are. Fruit's great, but it's salad, not dessert.
To the questions:
1. Pie. I have become a pie connoisseur and somewhat of an expert over the years. It all started when my mom would make everything but pie: apple crisp, peach cobbler, pumpkin custard (basically pumpkin pie without the crust!) I love all of those, too, but when I would ask for pie, I'd be told it's too much work. "No, it's not," I'd say. "It's totally worth it!" Mom's response: "Then you make it." So I did.
Currently blueberry and peach are leading the pack, but I love cream pies, too. Did a strawberry-rhubarb for the first time this spring and it was awesome. Blackberries are great, but almost gone now. I bake apple all through the fall, and pumpkin in the winter. Occasionally a lemon meringue - the one exception to my wife's chocolate rule - or key lime.
2. I probably make cookies more often than pie, but it's close.
3. Four or five nights a week. Mostly just a dish of ice cream, but pie at least once a month, and cookies every couple of weeks, as the spirit moves, or the wife & kids request.