Last night I spent about 40 minutes trying to get my uploaded map to align to the grid.
Problem
I just wanted the apps grid to align to the grid on the JPG. This was exceptionally hard to do. First I had to guess at what size to make the new map. Then I uploaded the JPG. Then I adjusted my the app's map size to be big enough. Then I had to scale up the JPG and then tweak it with the mouse to try and get it to align. Making this worse - whenever I moved the JPG, after I let go it would shift over several pixels. I could never get it to align.
Solution
I suggest that the grid be adjustable on the fly, with controls for positioning and size. This would allow for greater fidelity without adding much complexity. Instead of adjusting the base map, you adjust the grid.
Ideally this would be a toolbar that appears when the DM is adjusting objects on the map layer. Options would include:
* Grid size - the size of each square
* X Offset
* Y Offset
* Map Width
* Map Height
The controls could be editable numbers with scrubbable inputs (drag up or down for large number changes. click up or down for precise control).
Changes should be reflected in real time.
I'm happy to mock this up for you if my text doesn't make sense.