I was recently asked how I keep up with my coupons and track my spending. I do not have the best system, but it works for me. It is best described as organized chaos. On Sundays, I clip all the coupons. I sort them in piles of "keepers" and "traders" and a few specific ones that I give to a specific people. I then go through the ads, usually CVS and Walgreens and match the best deals from my stack of "keepers." I may do some shopping today or tomorrow after work, depending on time. Tomorrow I take my "traders" to work and swap with co-workers. All leftover coupons go in a folder with the ads. I repeat this on Wednesday with the grocery ads.
Also if I read a great deal on a blog, I immediately go through my coupons and match it up!
As for tracking my spending, I am still working on that. It is mostly chaos. No organization to it.