I feel that if I was going to buy raw milk from a very small scale operation that I would want to personally see their operation. You have to ensure that the farmers milking are really paying attention to what they're doing. I've had some particularly nasty food poisoning in my life, one instance of which landed me in the ER and had me on a quasi quarantine watch by the county CDC, in fact, and so I don't really play around with my food too much. Milk is a tough one because a healthy cow can become a sick cow overnight. It's also made more challenging by the daily goings-ons with the milking process.
Having said all of that, my wife and I buy raw milk from a mid-scale creamery in Los Angeles, near where my wife grew up, whenever we are in the area. I've never really had much concern over it, because this creamery has been in operation for many decades and is quite reputable, but we are also well aware of the risk.
People forget we pasteurize for a reason.
http://torontosun.com/news/provincial/raw-milk-dairy-farmer-...
At least that's how it worked in new Hampshire about 10 years ago.
http://torontosun.com/news/provincial/raw-milk-dairy-farmer-...
Source goes to jail.
An state level overview is here: http://www.realrawmilkfacts.com/raw-milk-regulations but certain local jurisdictions within each state may further limit sales.