Ad matching--Pain? Maybe sometimes, but for me I like it. I have done add matching at Best Buy AND Walmart. (sorry if you don't have these stores, maybe your area has a similar option?) There are catches to both. These are MY experiences:
Best Buy add matches to Amazon when it is SOLD and FULFILLED by Amazon. Also, they add match to box stores when the items are in stock.
Walmart, they are getting better. Cashiers now have an app on their phones to DOUBLE check your add match, making sure it's not a screen shot of something. This also is applicable to food ads for other grocery stores. So NO more carrying all those ads around trying to remember where the spot is in your ad you want to match! Also, in my area they now carry their own brand of milk that runs $1.99 ALL the time (just learned this, a few weeks ago)
GOOD luck with your Savings!