I am still figuring this out, but for some reason the software that I use includes any sugar added to the boil in the pre-boil gravity. This is not very convenient as I like to use this value as my target gravity during the mash.
Now for the sugar addition, it depends on your recipe. As some stated above, for Belgian style beers, strong ABV, it is recommended to add the sugar (usually 1 or 2 pounds for a 5g batch) during the fermentation, at high kreusen, a pound per day, boiled in water first. This is done for 2 reasons (that I can think of):
* you do not want to stress the yeast by giving it too much sugar to chew on at once.
* it will help dry out the beer and get a lower FG as you would if you added the sugar pre-boil.
Now, for a regular ale, when the recipe calls for some sugar during the boil, I add it before having a full boil, I bring the wort back to a rolling boil, and this is when I start my timer. I do not want to add it at the same time as the first hop addition, as it might stop the rolling boil.