Chicagolandia
I'll call this Hounding 101:

Hounding: to purchase something using little to no money. I think of it as hunting up the deals like a hound dog......

Each week, I start by checking in at my favorite locations: MSN message board Grocery Game followed by jillcataldo.com, then over to hotcouponworld.com. I start with the Grocery Game first because the information is the freshest, the scenarios have already been tested, and the ladies can always catch something that I miss. I next ventured over to jillcataldo.com - she's a local coupon queen that sets up deals, as do her followers, and she even links you to printable coupons to get the best deal. I love how thorough she is. Over at hotcouponworld, I get to view what deals have been done in stores across the country. They have a very comprehensive coupon database: this helps when planning what to focus on. I know we all have our basics like eggs that seldom have coupons, but to round out your pantry - hounding is the way to go.
Since June, I have paid less than $15 dollars in condiments (from salad dressing, to ketchup, to marinades, relish, mayo, etc.) in 6 months. I entertain 1-2 times a month, for as few as 6 or as many as 25. I haven't paid a dime out of pocket (OOP)for salad dressing, marinade, relish, mustard, and mayo since I got "serious" about couponing. Though there are coupons in the paper - I tend to find ones with higher values online. Though some smaller chain-grocery stores don't allow internet printables (IP's), I can still make it work for me. Manufacturer websites are a great place, along with coupons.com, smartsource.com, and couponloop.com to find internet printable coupons.
Like some of the pro's advise, I have a price book, I know the rock bottom price (the lowest price the item will see in a 3-6 month period) for many items I use, and whenever possible I wait for that price, and stock up when an item hits that price. If you have a separate freezer - this will benefit you the most. If you don't have a separate freezer, ask yourself this, would one work for your lifestyle? If so, save some of your coupon savings for said freezer. Remember, you can freeze bread, meat, chocolate, cheese, yogurt, premade meals, fruit, pie filling, etc.
Meat: if your local grocery store marks down their meat, clearanced meat can be a great deal. I tend to use it within 48 hours or freeze it until I need it. Mark downs can also include cheese (if you're lucky) and you can use coupons with marked down meat and cheese - works like a charm. Last summer, I stocked my freezer with loads of free or nearly free chicken (drummies and thights) from Meijer. They went on sale for $.59/ lb. got marked 40% off, and I had a $1 any Meijer chicken. As it didn't say whole chicken, boneless skinless chicken, etc., I used it on the cheapest possible item - smallest package (for highest savings), and even made a profit off of some of it. Most stores won't give you cash back, but you can use overage (if you have a coupon for $1 off an item that is selling for $.75, $.25 would be your overage) to help pay for other items, even tax!
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