Drawing Order in 2D Tile Editor

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I'm working on a tile editor for my game and ran into the problem of the order the images are drawn.

I want to allow the user to be able to draw to different layers (4 total) and to be able to move tiles forward or backwards in the order they are drawn, as in a graphics program like Photoshop.

Right now, the technique I'm working for is 4 different types, one with a pointer for each layer. The drawing order would be determined by the order that is contained in that type object. Therefore, I would have to use "Before" and "After" to re-sort the tiles everytime the position of one is changed. Has anybody encountered this sort of problem in a tile editor? In what way did you program it in order for it to be efficient and functional?

I'm doing this all in 2D. I know many people suggest using 3D sprites instead. Is the extra work to change from 2D to 3D worth it, or necessary, even? What advantages are there to each?