Today I downloaded a series of videos by Scott Ligon@MOCA Cleveland. Very interesting lectures. For a guy like me not school trained to peak in on this is cool. Why I say this, because the bucks involved to go to school, and the bucks involved in getting the software he knows and loves and uses, especially the industry standard Photoshop. Ultimately it about the tools themselves and not the brandname. You can have assess to whatever tools are available to you. BUT, the "working artist" are usually trained in Photoshop. This helps when you have to collaborate, share files, or move to a new company using the same software.
If you are not in the above professional loop or do not need the proware, or want to be well versed in many different software or are just starting out, use GIMP! Now, let me turn this around. If you are starting out use GIMP. Why, same or similar tools, zero cost. As you grow in your skills, for sure you will want the pro tools, or maybe not. MyPaint is wonderful too.
I am an Inkscape user, which is sort of like Adobe Illustrator. I like vector drawing because it is close to the CAD work I have used for years. Mostly you use a mouse but I guess you can get use to using a pen. For me using a pen is awkward. My Wacom Graphire 2 (man is that old) gave me a lot of issues. It was too small, as big as a mouse pad and the active area is small. Then on the laptop I had at the time it was jittery on the screen. On my newer laptop the display is solid.I solved the size problem by placing the digital tablet in an old laptop display lid. I used foamboard to fill in the sides and match the surface height. A clear sheet of flexible plastic makes the surface smooth. It is more comfortable to hold and pleasant to use. Maybe I will invest in an updated tablet.
Drawing vectors with a mouse is one way to draw, with a pen on a tablet is different. This is like using a pencil, you must really draw freehand. I have never been a good freehand drawer. The first thing I get is the blank page syndrome. Every artist gets this because you ain't been trained yet. SO, the next thing you must do is play like crazy, see what types of lines you can make. Practice drawing lines and shapes while you find a project you can work at. This will focus your play into skills. Video and pdf tutorials are great for freelance learners. Now you have something to draw, can you see it? draw it!
I noticed most programs use keyboard shortcuts, make a list, even incorporate them into a desktop screen so you can peak at them. I am thinking of a mini remote USB keyboard to mount on my tablet contraption so I won't have to reach for the laptop.
Now when doing vector drawing, it is one way of thinking. To do the same in raster or pixel drawing, there is another way. You have to learn how to apply the principles of art according to the kind of drawing. I went from pen-n-ink drafting to CAD with little trouble, then to vector drawing with no problem. Not having good freehand drawing skills is slowing my graphic tablet learning. I need to work at the concept, the muscle memory or hand-eye coordination thing and the workflow or procedures. In all I recommend Open Source Software artist tools to start.