I have been shopping for some time at the Homeland in Yukon, and worked at one in Norman about 10 yrs ago. Lets say you have 2 coupons for like items, they will double the first one, and the next one will be at face value.
I tend to just use coupons on things that are on sale there, and I also like to use the 1.00 off ones on other items, like toiletries, because it makes it cheaper than Walmart (I am talking 0.20 deoderant, or free on certain items) Others plan out by store, and hit sales at other stores (Williams is another option since they double up to 0.50, but it really depends on the sales)
I personally try to get all my shopping done (well most of it) once month. I don't have the time right now or the energy to spend the time getting super organized
One thing I recommend is at least keep a general idea of what you pay at your usual store with out coupons, that way you will know whether you are getting a good deal, because I think we all can agree most regular supermarkets are expensive! (Crest and Buyforless, are 2 of the most reasonable ones I know of)
I read The Complete Tightwad Gazette by Amy Dacyczyn, she recommends a notebook where you right down the things you buy frequently, sizes and such, and the prices at your usual store, and go around experimenting with different stores, writing down their prices too (and you could also figure the price per ounce in case you need to compare a different size), that way you can determine whether the sale price or price minus coupons is really saving money on things you typically buy (I have yet to try this, since doing this while dragging my kids along, would take too long) There are many times, I will pass up using a coupon if the generic is cheaper than the name brand with coupons.
SAHM of 5
Do not rob the poor because he is poor, And oppress not the afflicted at the gate.
For YHWH pleads their cause, And shall plunder those who plunder them. Prov. 22:22-23