I want to get a tablet soon in the hopes that it'll solve all my problems, give meaning to my dull existence, and give my art a more professional look. If you are a digital artist, or especially someone who has done both digital and traditional art, I'd love for you to share your tips and experiences.
Also, have some questions.
What new skills will I have to learn, and what skills carry over?
Is one type of art easier than the other?
Are my hopes correct or will they be shot down in pieces like the 1939 Polish air force?
Thanks in advance for any insight you can give me.

A shiny new tool isn't necessarily going to improve your artwork--practice, study, and experimentation will be your main help there.

As far as the questions go:
1)If you have a relatively firm grasp on fundamentals--anatomy, composition, color theory, etc., you can expect that those will carry over fairly well from traditional art to digital. However, your workflow will more than likely not translate as well, since the digital medium doesn't necessarily behave like traditional options. You will more than likely need to experiment with your digital tools to find a suitable workflow that fits the type of work you want to create--and it's best to have at least *some* idea of the type of work you want to produce.

2) They're different, though I will say I find digital art easier in the sense that I worry less about the tools and more about a solid idea. Not to mention, in spite of the rather sizable initial investment, it still doesn't hold a candle to the cost of my traditional art materials.

3) If you're hoping that the transition will be a smooth one, I wish you the best, because that isn't particularly likely. If you're expecting getting a digital tablet in and of itself to improve your art, you're also out of luck. However, if you establish some realistic expectations--after all, you're going to be messing around with a whole new toolset--then you'll be better set up for success.

Tips:
1. Transferring from traditional art to a pen tablet is hard at first. There's a big disconnect that you have to get over. Normally you're looking at your hand and the drawing at the same time, but with a tablet you're looking at your computer, and your hand is further down. It may not sound like much, but it takes a few weeks of practice to get used to.
2. Never forget the basics, they're important in every situation. To help with both these, you may want to start live figure drawing, available at virtually every junior college in america, for just a few bucks. Mine was like $20 for a full semester, not counting materials though.

What skills carry over? Almost all pencil/pen skills carry over, but you'll have to re-learn "how to use a pen" with the stylus. Should only take a few days' pracitce.
New skills to learn? Basic computer stuff, like saving every minute or so, instantiated saving, backing up data constantly, and depending on your software things like layers, blending effects, how to manipulate brushes, and saving-for-web.
Easy type of art? Art is as difficult as you make it really, but I'm a big advocate of learning how to draw life before you start learning how to draw super stylized stuff. Even picasso started off painting real life images before moving onto his signature stuff. If you start with that, everything else becomes easier.
Hopes correct? You mean like, hopes of becoming famous? Psh, I have no idea. It's just like "making it big" in the industry. It's 10% talent, 20% skill, 20% networking, and 50% luck.

IMO, traditional art seems easier to me. Something about a pencil and paper seems more fitting than a pen and tablet.

For traditional, practice drawing circles and squares. The circles will help out with your curvy lines and the squares will help out with your straight lines.

Also, use references, but don't trace. Try to freehand draw some simple images. Once you get good enough, try to draw something without using a reference

Thanks for all the in-depth responses, these things help me out.
For clarification, the hopes and dreams part was mostly a joke (except for the more professional look part), and I am a veteran pencil artist but very inexperienced with paint and color.
I'm also self-taught aside from some books and two semesters of art in high school that turned out to be more for beginners and didn't really help me out much. There's a few ingrained habits I'm trying to break as well such as never using references or tools like straight edges. Your professional tips help a bunch.
I'd upload some of my latest stuff so you could get a better idea of the skill level I'm at right now, but unfortunately it ain't furry.