I'm not exactly sure what the deal is with coupons here as I have never tried using them before. In general, from what I can tell from having gone to the states and whatnot, our grocery stores and such are fairly similar. I'll be living in an urban area with two grocery stores within 3 or 4 blocks, a third in the adjacent neighborhood, a fourth a short bus ride away, and some mom and pop/ethnic food marts not too far away as well!
Couponing is extremely different in Canada, let me tell you. We don't have a tiny fraction of the available coupons in the states, and also most stores won't let you combine coupons let alone double coupons like they will in the states. There also seem to be better coupons available in the states (more for dollar amounts than 50c off) and grocery prices are higher in Canada as well, for the most part. Result being that it's nearly impossible to get all the free stuff you can in the states, and it's difficult/impossible to make coupons worth your invested time. It's still a fun hobby for me though, and if I order (free) coupons every so often online and keep them in my wallet and watch for good sales, I can get things for a pretty good deal. You have to be really conscious of what a "good sale" actually is though, and you have to be willing to keep coupons around without using them until it's worth it, AND you have to use them only for things you would buy at regular price anyway....otherwise you can end up buying stuff you wouldn't have in the first place, making you lose money!
My pro tips -
1) know what a good price is, and for anything storable, only ever buy at that price and buy enough to last a few months. Sales come in cycles: for example, every 2-3 months you'll see boneless skinless chicken go on sale for 8.80/kg, and occasionally, maybe once a year you'll see it go for 6.59/kg. Throw some in the freezer. LOTS of things go through cycles like this with a regular "sale" price and sometimes a "superawesome sale" price. Like cheese will go on sale for 5$ every few months and 4$ occasionally (maybe every 6 months). triscuits go on for 2$ every few months and occasionally 1.50. The regular prices are usually at least 1$ higher. NOTE: be careful not to buy things only because they're at a good price and then never use them, that's my constant downfall.
2) for anything canned/packaged, find a discount store like food basics or price choppers and stock up. They can be as low as half price compared to loblaws and loeb! Even if you have to cab home the savings are often worth it if you do a big trip. Those stores often have awesome sales as well. Caveat: they usually have terrible-quality (but cheap) produce, buy at your own risk as it will often be bad the next day....
3) planning is awesome if you can do it. I can never stick to it. But at least have an idea of the things you're willing/able to cook, and the ingredients necessary. So like, if you know you have pasta at home, and ground beef goes on sale, perfect! you know you'll have a use for it. try to avoid buying too much fresh stuff at once if you're not positive you can eat it within a couple days - that's another of my downfalls. So much spoiled food because I never end up cooking that broccoli in time, or whatever.
4) despite the "not buying too much fresh at once", it's also bad to go to the store too often since every time you go you'll usually get a least a couple impulse things that you really didn't need, often unhealthy too. If you can manage to stick perfectly to a list (I can't) that's even better.
5) if possible, get a big chest freezer and use it for all your meat! meat can easily be double the price if you have to buy it at regular price instead of on sale. If you have a frozen stock of meat, you never have to buy at regular price. caveat: if you ever lose power for more than 24h or so, this sucks enormously. I know this way too well.
6) veggies always seem expensive for some reason, but it's usually cheaper to make your own food than buying the processed stuff. Especially if you do a giant batch and freeze it! Double-especially if you buy all the ingredients on sale. That said, I often buy the lean cuisines when they go on for 2$ because I love them, it's super fast,
relatively healthy (minus the salt) and it's only marginally more expensive than making it myself.