Stamping dollars goes like this> (1) Get to Bank for $1's, (2) Stamp them. (3) Get rid of the stamped $1's for large bills and quarters. (4) Back to bank to exchange: .25's, $5's, $10's. $20's for $1's. Repeat. It looks like this (below: Trodat 4913 )is the best option for a self inking stamp to get started stamping dollar bills. I would get two of these. Trodot 4913 ($14) self-inking stamp with up to 5 lines of text. We are going to put two lines on each stamp, one at the top, and one at the bottom. This gives you the option of stamping the top of a dollar bill and the bottom, and you can also do the front and back of each bill. The second stamp is so you have have 4 total messages for some variety. That should keep you stamping for the year. Cost should be $14 each. There is no cheaper flyering than stamping dollar bills! Yes Trodat 4913, comes with black ink, everyone will will need to get some red ink to make it stand out.