I want to make a counterpoint to the money role. The amount in your wallet could change on a daily basis. I find that could be a little more interesting then rolling for how much money you start with.
This could be a way to actually save money and have a little fun too. If you actually had to put the money from your wallet into a jar then at the end of your dare time you could treat yourself to something. Like for me, I only have $4 in my purse right now. So I wouldn't have much to choose from, but then I go to the grocery store and pull out $20 because I need to get $10 worth of gas. Now I have $14. This actually could be fun as a day clothing control. To keep it fun and manageable the clothing cost would have to be low and maybe even discount the price of everything by half if you decided not to wear underwear or spent a minimum of $10 that day.
OK! I love this idea and you should write another one like this for day clothing
if you don't, I kinda want to. PM me of you wanted anymore ideas or talk about it