The trick is to get into it so you learn the ropes, and then back off a bit. If you don't, you'll find yourself spending countless hours preparing and will get jaded by the whole process.
I personally rarely ever ad-match. I know Wal-Mart does it, but I try not to shop there anyway...so I go to multiple stores.
For toiletries, I've found the best thing to do is search the ads for items that are on sale, and combined with a coupon will be less than $1.00, or 1/4 of their normal price. For example: Suave body wash on a good sale is 99 cents a bottle. There are usually coupons for 25 cents off. Most grocery stores double or triple up to a dollar, so you could be paying 25-50 cents for a bottle, which normally costs $2.99.
Pharmacies like Wal-greens and CVS have their own type of in-store cash. Wal-greens are called Rapid Rewards and can be used on a subsequent purchase, usually a few days later and are good for like 2 weeks. CVS are called Extra Care Bucks ECBs. You can use them immediately on another transaction. For example, the promo may be something like this: if you a buy Band-Aid brand product for $2.99, you'll get $1.00 ECB. Combine a coupon of $1.00 off the Band-Aid product, and you total out of pocket for the Band-Aid item $1.99, and you have $1.00 to spend on something else.
There are often cash back deals on razors, body wash, all sorts of things at the pharmacy stores. Even Sonicare toothbrushes sometimes! And often, you'll pay less than 80% retail price for the item.
Sites like CouponSense or TheGroceryGame are great to get you going and to maximize your savings. You'll need 1 newspaper subscription for a family of 4 (don't pay more than $1.00/week per paper). And there are many coupons online that you can print from your home computer. Remember though, most stores will only accept one of each coupon per transaction. So if you print two, or receive two newspapers, you may only use one of each indentical coupon per transaction. So to get multiple items, you'll find yourself going through the checkout line twice, or splitting up your transactions.
To save money on produce, there are a few indoor farmers markets in the East Valley, that are open daily and have amazing deals on produce. There is also Bountiful Baskets and some local co-op gardening ventures.
If you eat meat, watch for the deals and buy and freeze. Chicken breasts under $1.50/lb is a good deal. Chicken thighs/drumsticks are often under $1.00/lb. And whole chickens under .80/lb. Buy ham during Easter or Christmas when it is .99/lb. Same for whole turkeys. You can get Foster Farms natural ground turkey at Costco for the best price I've seen it on sale...and it's almost always there.
After you've done it for a few months you'll start to recognize the deals and may find that you no longer need your subscription to the online site. Prepare you list, organize your clipped coupons, and stick to your list at the store. Watch your time. If after a month, it takes you more than an hour per store to prepare to go shopping...you'll need to change your approach.
After two years of it, I rarely coupon anymore. When we start to get low on our stockpile, I'll search the ads for the good deals and find coupons online. I cancelled our newspaper subscription because I don't use it often enough anymore, and it was such a waste of a natural resource and carbon emissions.
I've become a health nut. So most of my shopping is produce at the farmer's market. Some items at Sprouts, and I pick up a few regular items at Costco once a month. I don't buy many processed foods, and prepare most meals from scratch. Even w/o couponing, for my family of 4, we rarely spend more than $400/month. And we eat out twice a week (with coupons of course.) It's not just about saving money with coupons, its about buying items that are the right price and those that nourish your family.
Although I am the first to admit that there is occasionally a place for a box of mac n cheese in our kitchen....it's hardly nourishing, so as often as possible, I stay away from those items that though may be really cheap and even free with couponing, they are not helping my family in the long run.