I think it's extremely fitting that Elmore be featured on the cover of the last issue of Dragon.
I first started playing D&D in 1986, with the Basic and Expert sets that bore his artwork on the covers. Dragonlance was still new but popular and in full swing, and many of the modules that I purchased also featured Elmore's work. As a young teen, Elmore was my favourite fantasy artist by far, followed by Caldwell, Parkinson, and Easley. These were the artists, more than any others, that defined the look of D&D and heroic fantasy in my mind. Not just in their full-colour oil paintings, but also the black & white pencil and ink drawings in the interiors.
A year or two later, when I picked up the AD&D 1e hardcovers and some of the older modules, I was very disappointed with the production values. My Basic, Expert, and Companion sets all had Elmore oil paintings on the covers and interior art by Elmore and Easley. The AD&D books had these crappy low-budget sketches that were neither inspiring nor pleasing to look at. Obviously, I never really "got" Otus' art... I thought it was crappy when I was a kid, and I still don't like it. But I understand why many old-timers do. Just as Elmore defined the look of D&D for me, Otus defined the look of D&D for those who started playing it 5-10 years before me.
I don't have any data to back me up on this, but I would guess that more players discovered D&D in the mid-80s than discovered it in the late 70s. There are likely more players whose vision of D&D is defined by Elmore, Easley, and Caldwell than Otus and Trampier. These were the years when the Dragonlance and Forgotten Realms novels first appeared and made a big splash, and Elmore was the original artist that worked with Weis & Hickman in defining the look of the main characters.
Elmore is no longer my favourite artist; he has a wonderful eye for detail in his paintings, but I do find that his work feels rather static to me now (particularly his mid-90s and later work). I'll always have a fondness for his work however, simply because of how it defined to me what D&D should look like.