I have friends who have asked me to make websites and most are very small, usually I don't bother with a technical plan but one friend in particular clearly had goals larger than my own and the project is dragging on forever. If I had made a spec before the project I feel like this wouldn't have happened and our relationship would be as solid as before.
So my question is, how can you tell how small is too small? How do you tell when the project you're embarking on is going to end up in a guilt-ridden scope creep nightmare?