Specular Maps (what they do, how they work) are explained in the User Manual. (As well as bump maps.)
A specular map is simply the reflected color from indirect light. So, if the map has a color, this will be the 'reflected' color, if it's black, there will be no color reflected, if it's white it will be the reflected color (mixed with the diffuse color according to
fresnel's law* of reflections) (and white will be the part of the spec map most noticeable), if it's grey, then it will be noticeable in some degree relative to the lightness of the grey.
The specular map reflects light based on the shininess value you set for the material and the IOR... the higher the IOR the more noticeable reflections will become, and the higher the shininess value, the sharper the reflection will become... finally at shininess of 100000 it's about as sharp as you can get with Twilight. Shininess -for very rough surfaces I choose 7 or 10, usually I find myself going to "20" for very blurry reflections. Rarely do I use 10 or below... but I do use them. The Templates are great at default, so I only find myself changing shininess with Plastic>Shiny template to something like 600, 1500, 5000, 50000 sometimes, if sharper reflections are needed.
How to create specular map:
I basically manipulate the photo, based on how I want the reflections to happen, using many tricks I know in Photoshop (some of which you mentioned above) until I get the effect I want, knowing how specular maps work (as explained in the user manual, as well as what I've said in the paragraph above).
Sorry I can not be more specific but what I do totally depends on the image with which I am working. I find a combination of the Exposure, High Pass Filter, Invert, and the layer blend modes of Soft Light, Hard Light, Overlay, Screen, and Multiply are very useful. As well as using masks. Usually High Pass and Exposure and Levels gets me 90% to my goal.
*Fresnel reflection simply stated: reflection from a surface will increase with the angle of incidence... so when looking straight down (zero degrees) at a reflective surface, the reflection scene will be slight, but as you tilt the surface away from you (moving to 90 degrees), reflections in the surface will be much stronger.