The Grunwald Swords cover was certainly the easiest one that I ever did, as it went through the fewest iterations. Usually what happens is I'll have an idea for the cover, I'll block it out, and then find that I don't like it. So I'll scrap it for something else that I'll be happy with. Then I show it to Mary, who will give it the yay or the nay. Sometimes this results in me going at it again from scratch. And so on, until I end up with a cover that's half-way presentable.
But with this one, I had an idea; I executed it and liked it right away; I showed it to She Who Must Be Obeyed, and she liked it, too. Bam! Done in one! Well, that's never going to happen again.
I think part of it is that it's such a simple and straightforward design. There's nothing extraneous that clutters it up, and nothing that should really be added to it. There are three things I like to look for in a cover design: an emphasis on typography (check), a tightly-controlled color palette (in this case, green, black, and white: check), and some kind of visual hook (the swords; check).
What really brought it together though, and what was only apparent when Mary brought it to my attention, is that I was subconsciously patterning it after Disney title cards. My approach is a bit more minimalist, and less ornamental, but the general feel of the thing is there.
I think that classic, almost fairy-tale vibe exists as a sort of pop culture shorthand for the romance of the middle ages. That sense of chivalry and heroism is a big part of what drew me to the middle ages as a nerdy kid growing up in the Midwest, fueling a lifelong passion for the era. It wasn't very long before I saw that the clean, noble fantasy didn't hold water; the medieval period was dirty, disease-ridden, socially repressive, violent, and unjust. And, truth be told, all the more fascinating for it.
Still, that romantic illusion of gallantry and Once Upon a Time is a powerful one, and it's not like games set during the ACW put a bunch of amputees on the cover, or that games on Viet Nam use Nick Ut's "The Terror of War". It is a curious feature of wargames that they carefully sift out the horror and cruelty at the heart of every conflict. Now, what remains might be sober, serious, and enlightening, but the fact remains that our paper time machines never stop in at army hospitals, POW camps, and mass graves. We seldom have reason to; the horrors of war touch us in our hearts, while wargames engage and enrich our faculties of reason.
The packaging of the game, on the other hand, usually errs on the side of the romantic. This is true across the board; even "gritty" covers with close-ups of world-weary, unshaven soldiers, cigarettes dangling from their chapped lips, market in a very specific kind of masculine romanticism.