This is the right place to put it.
The disconnect is because you're not as skilled as your brain wants to think you are. It creates this awkward sensation.
The thing is, though, that feeling never really goes away for most people. Professionals and professional-level hobbyists just learn to work through it.
Look, I'm self taught. I can say for sure that lessons will help, but a lot of the time it's more in forcing you to focus your time and self rather than actual technique.
Because you know what? The more you draw, the better you get. Study or otherwise.
So if you're expecting that DVD to be that magic silver bullet that makes you have an "A-HA!" moment, prepare to be disappointed. You'll probably still look at a piece of paper or your Photoshop canvas meekly, and have no idea what you're doing.
And speaking of paper vs digital, use both. Carry a sketchbook everywhere and stop to "smell the roses", so to speak.
If some old guy catches your eye because he's dressed in a sharp looking suit, but he has this crazy eye patch, is looking around suspiciously and is holding a locked silver briefcase, draw him. Draw how you think he got there (perhaps an unfortunate accident with a pair of garden tools, a goat and the mafia), what he'll do next.
You know that kid you pass every day in town? Draw her.
Ever noticed what a weird shape that light is? What the hell, draw that too.
You don't need more than your daily walk (which you should be taking the time to go on) to get a library of sketches going. This will probably give you even more ideas, too, which might kinda suck at first if you don't know how to execute them, but will be gold when you get a little better (if you write them down).
Then, when you get home and have free time, open up Photoshop and have a little doodle in there, too. Draw something awesome, take your time to lament that you can't draw better, but then feel accomplished because you got as far as shoving some stuff down on the canvas. Draw it again with some studies and reference and you'll do better. Oh, and use your tablet as a mouse. Use it for browsing the internet, for whatever. That way you always have it out if you have an urge to paint or sketch, and you get the plus of learning to control it better without really thinking about it.
Now, back to studying.
Repeat after me: "The foundations" do not refer simply to painting techniques. It's best if you also focus on learning those while you learn the other stuff, but... you want to do character design? Design foundations, composition, and anatomy/dynamic anatomy/gesture may be of more worth to you at current. Make sure you're doing some figure or gesture work each day. More intensive anatomy studies are fantastic too. Work off photos and Artistic anatomy books.
Look out your window and mess with the composition of the landscape to make it more universally appealing. Work on minimalist designs, and see what moving junk around does. Give someone a landscape with a rounded composition, then give them a landscape where the composition is triangular and everything is jagged and sharp and ask which one they'd rather live in.
Oh, and draw what you want to draw, not what you think you have to. Don't draw 50 goddamn spoons and only that because the internet tells you. CtrlPaint is great, but you need some initiative. Take what you learned drawing that spoon (how curved metal reflects) and draw a massive fuckin' spaceship, or a guy who has a funny, very metallic hat.
Someone eating yoghurt.
http://www.floobynooby.com/pdfs/gesturedrawingforanimation.pdf (For animation, but helpful and inspiring for other types of dynamic static art. Buy an edited and typed and perfect version of this book here)
I guess the point is, even when you're feeling discouraged, draw through it. You have ideas, and that's more than a lot of people have. So just get them out. Never delete them, just re-iterate them after study. Maybe open a sketchbook here and promise yourself you'll post once a week: http://cghub.com/forum/forumdisplay.php?f=72
That's all I can say on the matter. Nothing will make you suddenly improve at a faster rate other than focused study and passion.
Good luck, and keep drawing. Hope my text-wall hasn't scared you too much, haha. Oh, and I wouldn't buy that DVD personally. It's all information you can get with a good Google search, though maybe not as intensive or well formatted.