Having studied the Desktop Wallpaper interface, I think I understand your response to my proposal. You have global settings for all images for a specific monitor (1, 2, etc.), not for specific images.
First, how about changing aspect ratio / resolution to "match image orientation to monitor orientation." Choose an image based on whether the x-axis is greater than the y-axis. Square images are always acceptable.
This implies, however, a change to the Image Mode. When this option is on, "Use 1 Image" becomes "Use 1 portrait image and 1 landscape image."
Looking at what I requested, it can be broken into two enhancements. The above was one, below is my thoughts on other part...
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Monitors don't necessarily have a unique ID
I was hopeful...
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The position can easily change and the orientation shouldn't matter.
This statement is true and false. The position can easily change, however most people never (or very rarely) move them around. I know people with home machines and many of our machines at work have dual monitors. Position rarely changes. However, if you have a laptop or a tablet, you are bound to plug it into two or more monitors (home, work, Mom's house, etc.) In my case, I have monitors in two different rooms of the house, and one at work. The one on my home desk is to the left. The one above the treadmill is above, and the one at work is to the left.
I know that the system provides you with position and dimensions, and tells you if it is monitor 1, 2, 3, etc. What do you think about taking the 1, 2, 3, etc and assigning it (optionally, of course), to a right, left, top, bottom, and main profile? That way if I plug into my treadmill monitor, I get the sports image and if I plug into work, I get the company logo, etc...
While auto-detection is (and would be) very cool, and it could work in many cases as outline above, another thought is to provide an option where the user tells DF that they have changed from one configuration to another. For example, when I plug in my table to any of these monitors, I have to click a tray icon for a menu and select a monitor scheme. That combined with "Match image orientation" would certainly satisfy me. In that case, you would simply have complete separate wallpaper data from each named scheme and you can switch via hot key, titlebar button, or tray icon menu.
Any of this sound interesting or doable to you?