This summer I finally made the leap to working digitally and I've discovered from my DM's and emails that many other artists have the same questions as I did. So I'm writing this as it might be helpful for those folks who are thinking of doing the same.
First, let's start with the hardware. After a bunch of research trying to decide between a Wacom Cintiq and an iPad Pro, I opted for the new 12.9" iPad Pro & Apple Pencil. I won't go crazy with tech specs, but for me the iPad was the better decision because it was more suited to how I wanted to work: It was more portable. I could access my Dropbox or Creative Cloud from it. I could use the camera to help make reference material. I was intrigued by many of the new drawing apps. And since an iPad does way more than just act as a drawing tablet, that was also very appealing. (ie: movies for my kids to watch on long car rides). I also went with the larger iPad because it's pretty much the same size as an 8.5"x11" piece of paper, which I normally sketch on anyways.
Secondly, the software. I use Adobe Sketch and Procreate quite often since they're both excellent for drawing and painting. I also use Astropad Studio quite a bit since it allows me to easily use Adobe Photoshop and Illustrator directly on the iPad. Basically it mirrors your desktop. Here's a review video that I found helpful. As for brushes, I use Kyle T. Webster's Photoshop brushes, and most of them also work in Sketch. I haven't tried making my own brushes yet, but I kind of feel like I won't need to because Kyle already did such a wonderful job with making them feel like traditional media.
How was the learning curve? Not bad at all. I was very worried about this because for the most part I've worked very traditionally up to this point: Sketch, scan, more sketching, more scanning, adjust sketch in Photoshop, paint, scan, send. Personality-wise I'm not one for easily introducing new things into my process but this was very natural. I was expecting it would take a few weeks before I felt comfortable enough to use it in my daily workflow, but it was only about 3 days. After a few weeks it felt like home.
How has it changed your workflow? It's streamlined it A LOT. If there's one thing I hate doing, it's scanning. I'm scared to guess how many hours of my career have been spent scanning. Since my sketches are now done on the iPad, it's eliminated at least half the scanning on any given project. How much I use it for final art varies as sometimes my finals are created 100% digitally, and other times it's approximately 50%.
How do you like drawing on glass? It was weird at first and kinda slippery, so I added a matte screen protector and it made a big difference. It added some tooth and now it feels more like paper. Have also been recommended this one by a few folks, but I haven't tried it yet.
Has it changed your work? The way I look at it is this is just another tool and it's up to me how much I want to use it, or how well I'll learn to use it. Generally speaking, if you want to change the look of your work, one way to do it is to change the tool. However, the work still comes from the same place so it still has the same voice. Overall my work still looks the same as it did before. Other than my process being streamlined, I do find I'm a bit looser now because I think about building projects differently as it's easier to mock-up an idea or try a new idea with less fear. I do miss the happy accidents that happen regularly when working traditionally, though. I do feel that over time I'll find the right balance, though.
I think that's it for now. If I think of anything else, I'll update this.
** Update: February 5, 2017
I've come across a few decent apps lately: Clip Studio - it's similar to Photoshop. Amaziograph, which is a pattern making app. It's very basic but strangely addictive. Graphic for iPad is a basic version of Adobe Illustrator. It's more like Ai than Adobe Draw is.