Here are some answers to your questions.
When you start gaming, as they call it, you will spend the same amount the first 4 to 6 weeks. The reason is even though you are getting that box of Cheerios for $2.25 you will buy 3 or 4 boxes to stock up. That is the crucial part--you are stocking up. You will do this for the first month to month and a half then you will do what the gamers call cherry picking.
It is funny, when you first get your list you are so excited. I remember coming in the door and telling my husband how much I spent and bringing in bags and bags of groceries. Then you hit week 8 and are kind of let down because you are only getting 9 or 10 things. The thrill of the hunt is kind of out of it. You have to deal, but you are saving tons of money.
I've compiled a list of tips to help you get started:
Cut ALL your coupons. Not just the ones you think you are going to use. The first couple weeks I only cut the coupons I thought I was going to use. Guess what? I could have gotten Hungry Jack boxed potatoes for FREE. Would I normally buy them? No. But free, I'll take and work them into a casserole any day of the week. I could have gotten glucose monitors free, razors free, cat food free and Cover Girl makeup free. Another reason is to trade. I never use Tide--I'm allergic. I also never use cat coupons, certain restaurant and others. Know what I get in return? Diaper coupons, stain fighters, yogurt, granola bars. All things we go through tons of in my house. What you do is get on a train once you join the Grocery Game. You and several others will trade coupons to your heart's content.
Shop alone. Seriously. All the saving money gurus tell you to and they aren't joking. You can't concentrate on what you are doing with munchkins. Sunday got away from me so I went Monday with my 1 year old. For some reason, I thought I could manage him, coupons and a cup of coffee. "Clean up on aisle 1!" That was me spilling my coffee. Again. Usually I go on Sunday morning and leave the kids at home with Daddy. I spend about an hour to an hour and a half cutting and organizing my coupons, getting my list ready then I'm out the door. I hit 3 stores which are all within the same block and I'm home.
Get organized. Nothing and I mean nothing will piss you off more than knowing you have a coupon for Tropicana OJ that will get you a carton for .69 and not being able to find the coupon. It'll happen. About 3 or 4 weeks into this you will have 200 to 300 coupons to manage. Yup you saw that right, 200 to 300. Some do the accordion file, some do individual envelopes. I have a 3 ring binder with trading card sleeves and use it. It is a life saver. My clipping, organizing and shopping go much quicker now.
So, you may ask, what are you doing with 12 Gillette Fusion razors and 6 glucose monitors and all that makeup that you didn't pay for? Easy. I sell it on ebay and pay for my Grocery Game fees. Not everyone knows you don't have to pay for these items, you know.