@AlexandreDesbiens I've added a screenshot from the only game I've played that seems to use it, however, a few others in the Ultima series used it as well.

You've illustrated exactly what I'm going for, but I still don't know quite how to achieve it. I could do a filled circle algorithm working outwards from a radius of 0 to 20 and then 20 to 30, ignore points already seen, and in the 20 to 30 range add them to a "green" list to choose my next point from, but that wouldn't scale very well if I wanted a map with say inner radius 30 and outer radius 400 as an example. Sorry if I didn't explain well, but I'm hoping to have this scale very well so I could set semi-random numbers for my map size, point count, minimum radius, and maximum radius.

That's all I could come up with as well, but after tiling edge colliders next to each other, I noticed they could cause the exact same effects as the box colliders so instead I've went with the second part of your suggestion which did take some time to script.. but I think is very worth it.

Are you just wanting to handle the current move only or do you want to be planning for future moves as well? Current move only, I'd suggest just brute forcing it as the resources required should be quite minimal.

Maybe not the right term for others, but if you were in C# with XNA, I'd assume you forgot to change your sampling state to PointClamp. What you describe regarding nearest-neighbor filtering when resizing should work just fine as long as you are scaling by whole value magnifications (x1, x2, x3, etc)