@K. A. Laherty That helps a ton, thanks. I definitely appreciate the slow and steady approach. So far, I'm focusing on shapes and gestures, instead of perceptive, proportions, and all that other advanced stuff. I'm totally not ignoring those completely, but shapes and gestures is what I judge myself the most critically on for the time being.
@Evolutionary Games - You see, I tried stuff like that, and I really hate to be the begging chooser, but I find it hard to generate images to my liking and in the style, I'm striving for. Perhaps I can use that stuff to generate assets for things I really don't care to put too much effort on, like random background objects, but using it primarily is not my current plan.
@ohmygiggles - It's a good thing I have a passion for game dev. I think that's the perfect place for me to try what you suggest. I'm definitely going to have more than a few art projects to work on in order to put what I'm working on together.
I've been thinking about this question, and what I came up with is two conditions. I should seek a tutor if:
1) No tutorial has been made that can help me do what I'm trying to do
2) I can't make much progress on my own.
Basically, for hyper specific stuff, that's when someone should seek a pro.