For reference, this piece was made around a year before "Crusaders of the Lost Mark".

Artist's description from Deviantart:

And here we have ourselves the feisty pegasus filly, Scootaloo! I think I had the most fun with her hair; I love drawing hair in general, but there's something extra fun with short hair styles. 8D But she was fun to draw in general anyway. c:

Anyhow, onward to her headcanon! D:<
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Scootaloo will be the second tallest of the CMC, and most likely remain the most lanky. Sweetie Belle around this age is slightly more awkward in body and as such a bit lanky, but Scootaloo never really does grow out of it. But that's completely okay, since it fits Scoots just fine. Scoots' pelt will be slightly darker than what it was when she was a filly, and as she grows older I figured she'd be a tiny bit sharp in appearance, such as pointier fangs than usual, pupil shape, and having very pointed ears. She also gets one of her ears pierced and loves to where the black wrappings around her front legs. As time goes on, her activities on her scooter and such will give her scars from time to time, but one that remains pretty visible is the one on her lower jaw.

The story behind that scar is that she got it when she got into a fight with a bully in middle school once. For whatever reason Scoots had come to school early that day, only to come across a group of "popular" kids really ripping into Sweetie Belle (whom was alone only because Apple Bloom couldn't go to school that day). The sight of one of her best friends cowering against the lockers in tears while being pushed and poked and mocked really struck Scoots' nerve, so before anyone knew what was happening she promptly punched the leader of the bullies in the face. It got into a scrap between the two, which was luckily broke up, but Scoots still got a scar on her face from it. I'm going with the bully being Diamond Tiara here, and if it is, the gal from that point on is wary of Scootaloo. o3o

Now, two of the things I'm often asked when it comes to Scoots are whether or not she can fly, and whether or not she is an orphan. After much mulling around, I've come to the headcanon that Scootaloo is indeed an orphan (this is why she doesn't have a parents headcanon linked above), and she cannot maintain sustained flight due to a disability with her wings. Scootaloo being an orphan doesn't bother her too much, due to her being in a very nice and loving foster home that really works to make things good for the foals they take care of (she lives with 3 other foals in the home, one being Pipsqueek).

As for her wings, they are strong enough to propel her forward on her scooter at great speed, hover for a short amount of time, and she can glide with them, but she can't actually fly with them. As seen in the canon show, this caused her a great deal of self-doubt and stress, but after Rainbow Dash's advice and the help of her friends, it doesn't bother her as much. At this age it stops bothering her almost completely.

Scootaloo's cutie mark is of a wrench with stylized wings sprouting from it (you can see the entire cutie mark HERE). The mark represents Scoot's love for building, assembling, and taking apart just about anything electronic. Specifically, it really highlights her ability to look at something that was once perceived to be useless or broken and build it into something better, sometimes by emphasizing what made the object be perceived as "useless" in the first place. It also represents that she's come to terms with the fact that she cannot maintain sustained flight and how she didn't allow her disability to keep her grounded. Despite not being able to fly, Scoots fully utilizes her wings, which still allow her to perform things that many ponies that CAN fly can't do. For example, she's among the best (and youngest) athletes at extreme freestyle scootering, making her one of the modern pioneers in making the sport more popular.

As said in Apple Bloom's post, she and the rest of the CMC have shifted their mission to helping young foals feel more comfortable in their skin and nurturing their talents, rather than doing missions for the sheer sake of hoping to gain a cutie mark (which they finally learned doesn’t work). It’s now more of a Big Sister/Brother, Little Sister/Brother club sort of thing.
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Aaaaaaaaaaaaaaand I think that'll do it for good ol' Scootaloo. If you have any questions feel free to ask me. And thanks a bunch for stopping by to take a look! C: