That raises my next question: how do you get multiples of the same coupon? Get multiple newspapers?

You have 5 $1.00 off 1 coupons that you use one each item you use. The $0.51 moneymaker is for each item:

“item is priced for $1.49 but there is a special where you get $1 off each item if you buy 5.”

1.49 x 5 items = 7.45
7.45 – 5 dollars = 2.45

“Use five (5) $1 off 1 coupons”

2.45 – 5.00 = $2.55 moneymaker

“item is priced for $1.49 but there is a special where you get $1 off each item if you buy 5.”

1.49 x 5 items = 7.45
7.45 – 5 dollars = 2.45

“If you have a $1 off 1 coupon, in this case it would work and the full $1 coupon will be taken off”

2.45 – 1.00 = 1.45

“since you bought 5 and got the instant rebate of $5 making the transaction a $0.51 money maker.”

you spend $1.45.
where does a profit of 51 cents come from?

One question: one big way you get through the challenge, particularly in the early days, is by employing ‘money makers’, that is, deals that end by giving you back money that you then put towards other things. I haven’t seen an entry listed yet that details the way you figure out money-making strategies and how, specifically, you stack various deals to make that happen. It seems like something a lot of stores would introduce policies to keep it from happening. If you could address this it would be a huge help towards me being able to institute my own $1 a day lifestyle!

I think everyone has a different system. I prefer to cut them out. If I have multiple copies of a coupon, I’ll use paper clips or staple them together so I don’t have individual coupons to sort through. I prefer to organize them into categories so they are basically ready to go when I shop. But I know many people who prefer to leave them in the flyers and just clip as needed. I just find that very difficult to manage, both in finding the coupons and then in cutting them out on the spot.

The main idea is to find a system that works well for you.