Hello, here are two quick and dirty articles you can look over and see whether raster or vector is better suited to what you want to do:
For detail I would lean towards raster (Photoshop or GIMP)
Your second link is absolutely fantastic, it should be stickied somewhere if it isn't already. Although I can draw just fine I feel like trying this "programmer art" out because I'm looking for a more "naive" style and it looks really great. Thanks.