Taking a flyer and building my abilities

Although I have done a lot of watercolor in my life I am switching to Oil Painting. I have not been comfortable in the past working with oils as it takes longer to dry and I haven't done too well mastering that. However, I took a flyer this time and decided to try it. I have been using them like watercolor lately. I am quite pleased with what has happened.
I have created a self-induced schedule of projects to get me to become a full time portrait artist. I did a study painting of my father's face. This wasn't complete but it was necessary as I needed to see if I could do what I wanted to do with oil paints. The piece is okay, but not completely up to my standards. Next I decided to do a still life. It is of fruit. I did it because I needed to know that I could paint textures and colors correctly. I must say this is turning out quite impressive.
I am going to start painting portraits next week. I have a plan to do three pieces to build up my portfolio. The first is a child, the second is a mayor, the third is a judge.
I also am seeking to find a way to do a candidate for the US Congress who is one of my friends.