I struggle with this too....people have no grasp of the time and energy that goes into decorated cookies so they balk at paying 2-3 dollars for ONE cookie. My husband works at a big plant with a bunch of guys and had an idea that I could make little bags of cookies and sell them to the guys there - he was thinking if I did decorated ones for Halloween or whatever, maybe they would want to pick one up for their kids or something....problem was, he was thinking I would be selling 3" decorated, wrapped MMF cookies for $1!!
I told him, thank you but no friggin' way!! We came to a bit of a compromise - I will make decorated 2.5" cookies and sell them bagged for $2 and then also sell 2 big fat regular cookies for $1 ( like chocolate chip, oatmeal, that sort of thing...) and we can go from there. He also suggested I make a cookie bouquet with some prices because they might want those or the company might want them for corporate gift-giving - which is all well and good but it's hard to price your stuff so your competitive but not giving it away.
I was concerned he would feel funny basically being the one charging that much for one cookie - I told him if he would be embarassed then don't do it. Hate to pass up a great opportunity but If I am spending hours upon hours sweating in the kitchen for $2 an hour after cost, what is the bloody point?