Given a $2$-dimensional space subdivided into $N\times N$ tiles, drawing a line from the edge's midpoint to the opposite field how can the $N$ tiles be found covering the majority of the line's path?
Is there a better way to this than computing the linear equation and iteratively advancing in tiny steps to check which bucket we fall on? If not what is the lower limit step size to choose?

You are lucky. I've spent weeks coming out with an algorithm for solving this type of problem. Here is how you should approach it: