Hi Jase!
Thank you for yet another awesome and helpful thread!
I've often said that there are members in my family that treat saving money like an Olympic sport. However, I agree that it can be a big pain in the patooey, especially when the coupons these days are something like "25 cents off 2 boxes of crackers," and the crackers are like $4 each.
I also get annoyed by those supposed rewards sites where you rack up "points" -- and then need 10 jillion points just to earn a dime off something.
The best thing I've found that works for me is to try to find places with regular built-in rewards. For example, some of the store chains here offer points for purchases that can be taken off your fuel bill, then run specials such as, 4 times the points for gift cards.
So if I buy a $25 gift card for someone's birthday, which I would do normally, I'll be credited 100 points, which equals $1 off per gallon for one time when I fill up my car.
Other helpful deals, if you have a no annual fee credit card and pay the balance off each month:
* I've taken advantage of introductory offers of 5% cash back in certain categories, and the regular card I use has 2% cash back.
* Target offers a 5% discount if you buy gift cards with their credit card.
* Many grocery chains here offer specials like Buy One Get One Free or things such as, Buy 3, Get 2 Free, Mix and Match. I tend to plan my entire grocery trip around trying to buy mostly things on sale if I can.
And the best thing is to stack the rewards if possible.
For instance, getting a Buy One, Get One Free, with a coupon, then buying a gift card during a 4 times the points special, getting enough points for $1 off per gallon for my gas, and putting every purchase on a credit card that earns an additional 2% cash back.
Just for kicks, I kept track of my rewards/redeemed points, etc. last year and it was about $1000 for the year.