First: see that list of blogs on the right hand side? You must go see Money Saving Mom right now. Crystal is a wonderful blogger and has her finger on the pulse of so many great deals out there. I highly recommend going to visit her blog and reading the CVS or Walgreens 101 posts. They are very good at explaining how this all works.
Done? Okay, great. I'm going to show you an example of how to use lots of different kinds of strategies all together to maximize your dollar at Walgreens. This week, there is a great register reward deal; a register reward is a coupon that spits out of the register when you buy the right combinations of goods. This week, if you buy three Reach toothbrushes or floss or 500 ml Listerine at 3/$9, you get a $6.00 register reward. All on its own it is a good deal; pay $9.50, get $6.00 back, making the items about two bucks each. However, There is a three dollar off three Reach/Listerine coupon from last week's newspaper inserts and you can use it to take three dollars off the total. What this means is, if you use that coupon, instead of $9.50, you pay $6.50 out of pocket, and get back $6.00 to spend on other things, making the cost per item effectively .13 each.
With that $6.00 register reward, you can then purchase other things that spit out other rewards. I used mine to get the following: ten packages Sharpie Accent highlighters, for which there are $1.00/1 Sharpie Accent highlighter coupons here (print as many as you like, I did ten); these highlighters are .99 this week, making them a .01 moneymaker. I also bought two packages of band-aids, using a .50 coupon on each. And I bought 6 packs of Bic pens, using a $1/2 printable coupon available in the blue bar on the right and in the Sunday newspaper coupon inserts. And finally, I used an in-store coupon for $2.00 off a package of Huggies wipes. I also used a weekly Walgreens coupons to buy memo books for .19 each (I use these for tracking my billable time and noting the weekly deals in the ads. After all coupons (printable, in-store, flyer, and newspaper) and the six dollar register reward I got from the Listerine/Reach transaction, I paid a little over five dollars for everything in the picture below. That wouldn't be bad all on its own, but then! Because I bought two Band-Aid boxes, I got another $4.00 register reward.
What will I do with all of this stuff? Use it, or donate it to my local elementary school.
If I were so inclined (and I might be), I could take the $4.00 off register reward, and do another Listerine/Reach deal, making my out of pocket $2.50 and getting me another $6.00 register reward. Which I could then use to do another Band Aid transaction.
It seems complex, but start small. What do you need this week? Highlighters? Then go, and get some free ones! Toothbrushes? Then go, pay six dollars, and get six dollars back to spend on other stuff you need!