For me, personally:
> what motivated you to learn to draw
Half of me wanted to impress my friends. The other half of me wanted to make stories come to life.
> what you were interested in drawing
Mostly animated characters. Faces. Portraits.
> biggest roadblock/weakness
PROPORTIONS. I hated how I'd draw something and it would always look "slightly off" but I couldn't really put my finger on exactly why
> how many times you've tried to learn
Probably about 3 times..
I discovered that although I can draw very well I have no visual memory. (For this reason it is actually very difficult for me to know who I'm talking to, even if I know them quite well.)
I've always loved to draw. It's relaxing. I watch cartoons. I wanted to be an animator when I was a growing up.
People, scenes, animals. Both realistic and stylized.
Time. Art is as much a trade as anything else. It takes constant practice to get good and maintain it. Software paid better than art.
I have a bachelor's of arts, in art. I would draw, paint, or create for 20+ hours a week, every week, for a couple years. I also have an associate of arts in graphic design.
Ultimately, I do not practice anymore because I love programming too, it pays better, and there isn't enough time in the day to be great at both.