We have a teacher who works at one of the local bars a few towns over. He only works on weekends, but he said he can make about half his annual salary in tips just from working during the summer and some weekends through the year. I really do think if you manage things well it can work, but you have to be smart and disciplined. I was looking at the healthcare portal the other day trying to figure out what my monthly hit would be like if I needed it. Looked like about $1200 per month for the top plan, but I wasn't sure if I was reading it right.