Is this someone who will bring in lots of other cookie customers in the future for you?
I'm in the same tough place, in June I have to make 48 4in cookies wrapped and bowed. I hand made the cutter by the dalmation picture she gave me, and I said $2.00 as she started to say $1.00 each. She took the $2.00 price but I have to consider that she is a supervisor of mine and word of mouth where I work is everything.
I do plan on cutting back on some of the fine detail work that I originally had planned so that it will be worth more than $2.00 but I won't be slaving over them for days either.
What is the complexity of the design you will be doing? Is this person a family friend who is a repeat customer? It's possible to say its an introductory sale price or a special price for cake buyers only etc.
Be careful not to underprice yourself to much, times are really tough and we are paying a ton for gas and food right now and if the grocery stores are charging us more than your going to end up cutting into supporting your household budget. Flour, eggs, and butter have all gone up lately.
I do know someone a couple weeks ago had made up a cutter for a 3in 4in and 5in cookie hoping they would choose the 5 in design and they ended up picking the 3in design for $1 a cookie
not only was the design beautiful but by the time your done baking, mixing and supplies you've spent $20 in electricity, ingredients and such.
I would say if you new to cookies go for $3.00-$3.75 until you have a more experience, and make sure you post the pictures here