~ can winning several dozen dollars become the happiest day of your life? ~
Sure it can. I remember times when $20/month was considered a good salary where I lived. But, of course, several dozen dollars won't make you that happy if you make $500 per day. I think it's that simple. In reality, only few people make $500 per day around the world, so, most people would be happy to win 50-60 dollars, especially if the bet was under $0.50.