I had this question too when I started couponing. I would see people getting things for free or nearly free and while I could do that with certain items like toothpaste, bodywash etc...what about things like food? or toilet paper? etc! Those items are harder to get and I always worried that I was paying too much and should wait for a better deal!
So I decided that I would write down my normal prices for these items...and if I could cut that price in half with a deal or Q then it was a "good" deal so go for it...but if I could take it under half price..way under....it was a "great" deal so stock up! I figured it may not be free but I am spending at least half what I would have...so that's an awesome savings 
Keeping track of what you spend on something and when you get sales/deals and you will start to see a pattern of when things go on sale...and have a bottom line price you'll pay on those items. I do this with toilet paper and laundry soap....I know how much per load or per roll I am willing to pay and when I see a deal that will make it that cheap (or cheaper!) I go for it!
Good luck!
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