Edge detection / angle

Question 1

If you're writing your own library, then creating a robust solution for this problem will allow you to develop several independent chunks of code that you can string together to solve other problems, too. I'll assume that you want to find the corners of the checkerboard under arbitrary rotation, under varying lighting conditions, in the presence of image noise, with a little nonlinear pincushion/barrel distortion, and so on.

Although there are simple kernel-based techniques to find whole pixels as edge pixels, when working with filled polygons you'll want to favor algorithms that can find edges with sub-pixel accuracy so that you can perform accurate line fits. Even though the gradient from dark square to white square crosses several pixels, the "true" edge will be found at some sub-pixel point, and very likely not the point you'd guess by manually clicking.

I tried to provide a simple summary of edge finding in this older SO post: what is the relationship between image edges and gradient?

For problems like yours, a robust solution is to find edge points along the dark-to-light transitions with sub-pixel accuracy, then fit lines to the edge points, and use the line angles. If you are processing a true camera image, and if there is an uncorrected radial distortion in the image, then there are some potential problems with measurement accuracy, but we'll ignore those.

If you want to find an accurate fit for an edge, then it'd be great to scan for sub-pixel edges in a direction perpendicular to that edge. That presupposes that we have some reasonable estimate of the edge direction to begin with. We can first find a rough estimate of the edge orientation, then perform an accurate line fit.

The algorithm below may appear to have too many steps, but my purpose is point out how to provide a robust solution.

Perform a few iterations of erosion on black pixels to separate the black boxes from one another.
Run a connected components algorithm (blob-finding algorithm) to find the eroded black squares.
Identify the center (x,y) point of each eroded square as well as the (x,y) end points defining the major and minor axes.
Maintain the data for each square in a structure that has the total area in pixels, the center (x,y) point, the (x,y) points of the major and minor axes, etc.
As needed, eliminate all components (blobs) that are too small. For example, you would want to exclude all "salt and pepper" noise blobs. You might also temporarily ignore checkboard squares that are cut off by the image edges--we can return to those later.

Then you'll loop through your list of blobs and do the following for each blob:

Determine the direction roughly perpendicular to the edges of the checkerboard square. How you accomplish this depends in part on what data you calculate when you run your connected components algorithm. In a general-purpose image processing library, a standard connected components algorithm will determine dozens of properties and measurements for each individual blob: area, roundness, major axis direction, minor axis direction, end points of the major and minor axis, etc. For rectangular figures, it can be sufficient to calculate the topmost, leftmost, rightmost, and bottommost points, as these will define the four corners.
Generate edge scans in the direction roughly perpendicular to the edges. These must be performed on the original, unmodified image. This generally assumes you have bilinear interpolation implemented to find the grayscale values of sub-pixel (x,y) points such as (100.35, 25.72) since your scan lines won't fall exactly on whole pixels.
Use a sub-pixel edge point finding technique. In general, you'll perform a curve fit to the edge points in the direction of the scan, then find the real-valued (x,y) point at maximum gradient. That's the edge point.
Store all sub-pixel edge points in a list/array/collection.
Generate line fits for the edge points. These can use Hough, RANSAC, least squares, or other techniques.
From the line equations for each of your four line fits, calculate the line angle.

That algorithm finds the angles independently for each black checkerboard square. It may be overkill for this one application, but if you're developing a library maybe it'll give you some ideas about what sub-algorithms to implement and how to structure them. For example, the algorithm would rely on implementations of these techniques:

Image morphology (e.g. erode, dilate, close, open, ...)
Kernel operations to implement morphology
Thresholding to binarize an image -- the Otsu method is worth checking out
Connected components algorithm (a.k.a blob finding, or the OpenCV contours function)
Data structure for blob
Moment calculations for blob data
Bilinear interpolation to find sub-pixel (x,y) values
A linear ray-scanning technique to find (x,y) gray values along a specific direction (which will also rely on bilinear interpolation)
A curve fitting technique and means to determine steepest tangent to find edge points
Robust line fit technique: Hough, RANSAC, and/or least squares
Data structure for line equation, related functions

All that said, if you're willing to settle for a slight loss of accuracy, and if you know that the image does not suffer from radial distortion, etc., and if you just need to find the angle of the parallel lines defined by all checkboard edges, then you might try..

Simple kernel-based edge point finding technique (Laplacian on Gaussian-smoothed image)
Hough line fit to edge points
Choose the two line fits with the greatest number of votes, which should be one set of horizontal-ish lines and the other set of vertical-ish lines

There are also other techniques that are less accurate but easier to implement:

Use a kernel-based corner-finding operator
Find the angles between corner points.

And so on and so on. As you're developing your library and creating robust implementations of standalone functions that you can string together to create application-specific solutions, you're likely to find that robust solutions rely on more steps than you would have guessed, but it'll also be more clear what the failure mode will be at each incremental step, and how to address that failure mode.

Question 2

Can I ask, what C++ library are you using to code this?

Jerry is right, if you actually apply a threshold to the image it would be in 2bit, black OR white. What you may have applied is a kind of limiter instead.

You can make a threshold function (if you're coding the image processing yourself) by applying the limiter you may have been using and then turning all non-white pixels black. If you have the right settings, the squares should be isolated and you will be able to calculate the angle.

Once this is done you can use a path finding algorithm to find some edge, any edge will do. If you find a more or less straight path, you can use the extreme points as you are doing now to determine the angle. Since the checker-board rotation is only relevant within 90 degrees, your angle should be modulo 90 degrees or pi over 2 radians.

Question 3

I'm not sure it's (anywhere close to) the right answer, but my immediate reaction would be to threshold twice: once where anything but black is treated as white, and once where anything but white is treated as black.

Find the angle for each, then interpolate between the two angles.

Question 4

Your problem have few solutions but all have one very important issue which you seem to neglect. Note: When you are trying to make geometrical calculation in the image, the points you use must be as far as possible one from the other. You are taking 2 points inside a single square. Those points are very close one to another, so a slight error in pixel location of of the points leads to a large error in the angle. Why do you use only a single square, when you have many squares in the image? Here are few solutions:

Find the line angle of every square. You have at least 9 squares in the image, 4 lines in each square which give you total of 36 angles (18 will be roughly at 3[deg] and 18 will be ~93[deg]). Remove the 90[degrees] and you get 36 different measurements of the angle. Sort them and take the average of the middle 30 (disregarding the lower 3 and higher 3 measurements). This will give you an accurate result
Second solution, find the left extreme point of the leftmost square and the right extreme point of the rightmost square. Now calculate the angle between them. The result will be much more accurate because the points are far away.
A third algorithm which will give you accurate results because it doesn't involve finding any points and no need for thresholding. Just smooth the image, calculate gradients in X and Y directions (gx,gy), calculate the angle of the gradient in each pixel atan(gy,gx) and make histogram of the angles. You will have 2 significant peaks near the 3[deg] and 93[deg]. Just find the peaks by searching the maximum in the histogram. This will work even if you have a lot of noise in the image, even with antialising and jpg artifacts, and even if you have other drawings on the image. But remember, you must smooth the image a lot before calculating the derivatives.