You know, I like 5, 7, and 9 the best, and in that order. They all strike me as very clean. I have some comments about them, but one thing to keep in mind is that I'm colorblind. How bad? Until late in high school I thought giraffes were green. I found out otherwise in an incredibly embarrassing fashion.
I like 5 the best overall. The thing that bothers me most about it are the "N"s. They look like pi, and when I look at it I almost want to say "Dupgeops and Dragops". For whatever reason the dots in the "O"s are fine, despite the resemblance to capital theta. I prefer the dots in the "O"s to be just a little more substantial or else not present, although maybe this would conflict with the lighter typeface. I like the upper and lower lines which set the vertical extent of the text. The ampersand is conveniently placed so that it is clearly part of the read text, although I don't mind it off to the side either. I would want to play around with the lettering so the offset between the letters of the top and bottom isn't quite so distinct. That is, both lines end with "ONS" but the offset between them isn't pleasing to my eye. If the top is meant to be centered with "& DRAGONS" my eye doesn't catch it, and sees the asymmetry instead. Working a bit with the ampersand and/or the tracking could probably fix this. Finally, I love the stylized ampersand with the breath weapon. Love it. You should pass on kudos to Emi for that alone. I like its appearance in all of 1, 5, 9 and 12.
I think 7 is a close second, and I do dig the dull metallic look that almost has a shape like the edges of a sword with a very small fuller, which I find quite appropriate. There is some danger of reminding the viewer of brushed metal, which has fallen into disfavor since its overuse in the mid 2000s, but for lettering I'm not sure it's such an issue. The lettering isn't as distinctly readable as 5 is to my eye, but I'm not quite sure why that's the case. It may be as simple as the lesser contrast from the white background. The dividing line is also nice, and has a clear inheritance from the 3e and 4e logos, although I think I prefer the version in 5. I miss the breath weapon on the ampersand. Adding a dull red breath weapon that caused a reddish glint on the parts of the letters which "face" the ampersand might be very cool, assuming it could be done so the metallic/red contrast wasn't distracting. A non-red breath weapon might be more appropriate in that case. A tough call.
The last one I quite like is 9, which is probably closest to the current 4e logo. The very small kerning for "DU" and "NS" is distracting for me, and doesn't give the letters the whitespace present in the current logo, which I think is important for readability. I again like the stylized breath-weapon ampersand, and especially its more prominent role in the logo. I think I miss both the dividing lines and the dots in the "O"s.
I'm really enjoying these articles, Jon, and it's heartening to see you on these forums as well.
If there is an "iconic" artist for 5e I'd like to put in another vote for Komarck. After viewing his images I almost always wish I could zoom in to see the details better, and zoom out to answer the questions the image raises. For fantasy art it's hard to ask for more. The illos of the Gith are pretty amazing. And the
cover to Dungeonscape is fantastic. In particular, that is the best beholder I think I've seen anywhere. It's not silly, it's terrifying, and for the beholder that can be quite a feat.
I'd also like to see more Justin Sweet. His
character portraits for Icewind Dale 2 are my favorite in any fantasy game. They are grim and contemplative, which I find a nice change of pace to the endlessly posturing badass that is more typical. I reuse those images all the time. I'm also partial to stuff like
this. His works tend to be more somber and dreamlike, as others have mentioned, but he can really nail those qualities. I'd love to see his interpretation of some of the lower planes.