Every visual representation that you see starts with one that has already existed (such as the paper, images of creatures, etc), and so the challenge (besides writing a fun description/analysis that explores the creature) is arranging and utilizing everything in such a way that it looks fresh, and feels authentic.
Not being a top of the line artist creates added limitations, as it effects more so what I can present, but it also means I can explore different alternatives. When I first created the Red Brambleback, the text description was already provided by Sharjo, but how I was going to create an artistic representation of the creature was completely up in the air. I could have tried to draw them, but I quickly found photocopying wasn't my friend, and my skills with a mouse was not enough to create something appealing.
When looking for reference images, I had found the model image with a blue background that Surrender@20 had posted, and I came up with an idea that kind of defined what people think of as far as the journal entries go. The program I was using (GIMP) had a "Select by Color" tool, which helped with not only getting rid of unwanted backgrounds, but posed the basis for the "ink drawings" of the creatures. By selecting several colors on the image I found on Surrender@20, and painting over it in black, it looked like a fairly authentic ink drawing of the Brambleback!
As I kept doing these, I slowly got better and more efficient on how I did things (being able to invert the selection to clear away anything unwanted when making the creature images, until a lot of people requested Gromp. Gromp proved to be exceedingly difficult for creating the "artist representation", because the one image I could find (that would work with what I could do at the time) was one with his tongue phasing through his face. Additionally, the way my Color Selection tool recognized the colors was a bit different, making it difficult to get a working profile of him.
I eventually overcame this by doing some slight editing near his mouth, and altered the Color Selection so that its recognition of colors was a bit simpler, making it easier to get a working image, more or less. From there, it was pretty consistent, although I desperately wanted to add in extra things: bark from the Brambleback, a mushroom from Gromp, fur from Murk Wolves, or even feathers from the Razorbeaks. There was simply no resources that I could use though, so I had to settle a bit.
The paper background I rolled with eventually drove me crazy, because there was ink in the bottom left, and top right corners, as well as a simple pair of spectacles or something, but I had to keep rolling with it. When it came to the Dragon though, which would have more pages, I knew I couldn't get away with it. So I played with some tricks of sort.
By this point my editing skills have gotten better, not good enough to cut out the top right corner and patch the paper, but better. I was able to edit out the single scale from the Dragonslayer promotion, and by overlaying a bunch of copies, it made a nice sheet of dragon scales which I could lay over the top right corner.
I won't reveal "all" of my tricks, but I do want to explain the photograph slightly. I figured the world of Valoran had cameras, as Zac's teaser and reveal had old time photographs, so it was justifiable to add one in myself. The picture was a frame from the Work in Progress reveal of Summoner's Rift, and then I had used a screenshot of Prehistoric Anivia's egg form for the dragon baby. With a few filters, and touch ups, I had a working old-timey photo of a dragon protecting its offspring.
I think doing the Dragon, and planning out Baron Nashor has made me want to branch out a bit more, and up the quality, as these creatures are the bosses. I did several more ink representations, additional pages, and some added "wow" factors like scales, photographs, and burn marks. Maybe as I learn more tricks, and build up some resources, I'll be able to do more things, or even go back and touch up old ones.
Gosh, sorry if I went on about this too much. I hope I explained myself well enough, and I'm glad to have created something that both the community, Rioters, and myself enjoy. I'd love to see Riot do something similar one day, perhaps. I think there's a lot of potential with the resources you guys have vs those that I have, but it doesn't make what I do any less enjoyable in the meantime ^_^