Fine art major here. Originally I was a digital art major but I felt so intimidated by people who lived and created in these programs while I was having a hard time keeping up and grasping how to use them. You'd be surprised how much of your latent fine art skills are transferable. Treat digital art as simply a new medium.
Now after years and years of staying away from digital art, I'm currently working on the first chapter of my webcomic and here are a few things that helped me transition from traditional to digital.
Hardware and software:
A drawing tablet really helps especially if you're used to traditional art so it's great that you're getting one for Christmas. However, if it doesn't feel right, don't feel bad about swapping it out for another. You can go with ones that have built in screens or surface tablets ( like the one I use a medium wacom intuos 5 touch.)
If you're not used to looking up from your drawing surface while drawing, a surface tablet might take some getting used to whereas you can treat a screen tablet like you would a drawing surface. My S/O also got me a new tablet for Christmas but we returned it for several reasons. While it was a nice gesture, my tablet is my work station so I'm very particular about its specifications and my current one works fine so no need to replace it. There were no hard feelings and I'm glad he gave it to me early just to make sure.
If you're ever looking for a replacement..Tablets can get pricy but I always recommend looking for used ones as it's an item that tends to get resold by it's user at some point. I bought mine 10 years ago and am JUST now making use of it.
As far as software. I currently use a "totally" legitimate copy of photoshop cs6, and it's taken a few weeks of playing around with it to feel more comfortable with using the program. I highly recommend downloading additional fonts and brushes before you start any projects as most programs will be pretty vanilla as far as features.
There are plenty of software options though, so look into what will work best for you and what's in your budget. Watching some tutorials on basic program features really helps you learn the hotkeys as well.
Expectations:
It's not going to be easy and you might find some challenges along the way but don't get discouraged if what you're trying to create isn't turning out quite right. Just like traditional art, practice makes perfect so start with some side projects, commissions or practice pieces to get more comfortable in the digital setting.
Hope this was helpful.