There was a question on Quora asking for advice from going from traditional art to digital, and I thought I would weigh in, but first realize that the beginning of this post addresses another Quora member who burned calories to answer the question saying he couldn't answer the question because it would would involve way too to much time and effort. Here goes:
To the person that said the question is massive and would require an answer based on a huge amount of time and information, you are making a novel out of a Fortune Cookie question. Such advice only needs to be as long or as short as it needs to be. In my case, I often turn fortune cookie answers into ones that get the TL/DR response. So here is my TL/DR response.
To start out, ask this question, “What would I want to tell myself if I was just breaking into Digital Art for the very first time?” Here’s a list of some advice I would like to receive.
First, your instincts are correct, get a tablet. I use a Wacom Tablet and got my first one before the 21st Century. The main one I use now is a Cintiq. Whatever you do get, it doesn’t have to be the biggest or best tablet, but it should be one commiserate with the type of strokes and gestures you make on regular paper. So, if you use large flourishing strokes, don’t get a small tablet.
Not all tablets are created equal. Do your research. Generally speaking, if it seems too good to be true, it probably is. So if someone is offering you a tablet that is big with multiple levels of pressure sensitivity for a very low price, read the reviews on it carefully. You should be doing that anyhow.
Get the best computer you can, so yeah, fastest and most powerful one you can afford. Depending on the type of application, you want to get enough heft and power behind it so that you aren’t dealing with a lot of lag, and a lot of things in a drawing application can lead to lag. Add to that the multi-tasking aspect of computers and you could slow your computer way down. I love to listen to audio-books and even that slows things down from time to time. If you watch videos on your computer while drawing, this could also be a bit of a problem unless you have a computer up to the task.
Don’t be too hard on yourself about the learning curve. If you get a tablet without a screen there is that surreal disconnect of drawing while looking up at a screen. This will take some getting used to. There will also be getting used to the texture and nuance of drawing on a screen, but will be a little less. Still, be patient.
Layers are your friend. One of the advantages of digital art is the ability to add layers that isolate parts of your art from others. Enjoy those. If you want, you can duplicate them, experiment, and then if you don’t like result, delete or undo. The fun of digital is that you can try out a lot of new things without wasting materials like paint, canvas, and cleaning a lot of brushes, or finding yourself having to restock a lot of colored pencils, pastels, and other materials.
Save often. Save multiple versions of your work. If the app has the ability to auto-save after a certain interval, then do it. I love using Corel Painter 2018, but found myself losing thirty minutes of work after getting in the zone and forgetting to save only to have Painter Crash on my mac. What is most concerning is that there was an Auto-save feature at one time in Painter, but they took it out. You should always save when you feel unsure about how something will turn out. So, maybe you are about to merge or collapse layers, or turn a another type layer into a default layer from another type of layer, that is a good time to save.
Enjoy the instant aspect of digital. You fire up the computer and your ready. There is no cleaning of brushes, there is no setting up and getting the right lighting (unless your working from live reference). You don’t have to stretch a canvas, prepare your medium. You might however have to wait as your application launches…and spins indefinitely.
Flip the drawing often. One of our problems as artists, and I include myself in that broad term, is that we can’t see the distortion we make in certain drawings. When we flip it, it becomes apparent quickly. So do this often. You will save yourself a lot of pain and effort the more you look at things from a different perspective.
Experiment with different applications. Learn the strengths and weaknesses of the different applications and don’t be afraid to use different ones depending on the type or results you want. Use a vector program for illustration or for smooth lines that can be resized easily. Use a raster program like Photoshop for more painterly digital art. Corel Painter if you like natural media. If you don’t have a large budget, then get the free alternatives to those programs that open source offers.
Get multiple monitors. I used to have three, including my Cintiq, but one of them stopped working a couple months back. It worked since about 2007, so it was a good twelve years that it worked for me. But I only started to groove on multiple monitors a couple years ago. I would use one for the application, and another for reference, and still another for watching/listening to videos.
So there's ten tips from moving from traditional to digital. If you find yourself favoring one form over the other, then my advice is enjoy each for what they are. I still love to draw using my sketch pad.
If your moving to digital from traditional art, you will find there is a tradeoff. I just hope you find it as fun as I have over the years.