O.K. - for nuts and bolts / set screws it's best to divide 'em up by diameter first! For the small sizes, you will get all the different lengths in one drawer, so do that! As the sizes get bigger, you will need seperate drawers for bolts and nuts/washers, and for the really big sizes you will need a couple of drawers for the bolts!
I have one cabinet for regular nuts and bolts, another for cap screws / grub screws and machine screws and a third for woodscrews. Each cabinet has colour coded labels - blue for British Standard, green for Unified and red for Metric! If I wasn't sat on my backside in a foreign hotel this week I'd attach pics!
Start by acquiring a few boxes of the sizes you are likely to use most - firms such as MSC are a good place to start if you have them in Canada, especially their specials flyer! If the opportunity comes up to acquire surplus fasteners in a job lot then grab it, provided the price seems reasonable!
For woodscrews, I sort by length first, and the gauge!
Enjoy....