Yeah, scouting can appear a little abstract at first, I think in older versions of the game it was more of a micro management thing, then it was redesigned to be more macro management. I'll give take a stab at answering what I can based on what I understand.
So on this screen, you'll see the levels of your coverage for each country as you cycle through the list on the drop down:
You can see the difference in this screenshot from the above one that my Canadian scouting coverage is not as good as my scouting coverage of the USA - that can be for a few reasons, however, in this instance it is because I do not have as many Canadian scouts as I do for the USA, which you can see from the highlighted areas.
So to solve this, I would go onto the hire scouts tab, shown here, and then I would go to the drop down on the right hand side, highlighted, change it to Canada to show me all scouts based in Canada - I personally then like to sort the column for 'Potential' by clicking on it and that will rank them in order of highest to lowest. Then make a few signings from that list and watch the number underneath each province in Canada go up.
(if you have the scouting boost of +5 active in the monthly spending then the number will show 20/20 at max, however if you do not have the monthly spending scouting boost active at +5 then it could be anywhere from 13/20 (for the -2 option) to 20/20)
Hopefully that helps on one of the questions.