Can someone who knows about VTT explain how to convert paper maps?

[Neyjour]

Okay, hmmm... with the size not being divisible by 100, I'm not really sure how to make it work properly.

The only thing I can think of is to "stretch and squish" them (resizing by unlocking the aspect ratio). So for example, the winecellar would be resized to 1600x1200 instead of the current 1584x1224. The differences are small enough that you really can't see the distortion. I doubt anyone would even notice...

I'm attaching an example for you to compare, with a 100x100 grid dropped on top.

Do you have larger resolutions of these? If you do, start with the largest resolution you've got and try this method of resizing to get a number divisible by 100. And go either up or down depending on which direction is the least amount. Like for the width of the winecellar, I resized up by 16 pixels rather than down by 84. And for the height, I resized down by 24 instead of up by 76. Once you've got that done, then just start experimenting with resizing the map down (always keeping it divisible by 100) until the scale looks right (1 square = 100x100 pix = 5 feet).

EDIT: And you'll want to do this with the clean version, that doesn't have your original grid on it. So once you've got the correct dimensions, you'll save it as your ungridded map, and then lay your new 100x100 grid on top for the grid version. I like to do my grids like you've done here, with the grid on the floor (under all the objects and such) instead of on top of everything. It would be kind of tedious and time-consuming, but you could use a soft eraser brush to erase the grid lines where they fall on top of the objects, walls, etc. Then when you're done, merge the two layers and save as a .JPG.