Did this 3 years ago when I broke out on my own. I'm in Boston. MA has a decent portal through their MA Health Connector site. For my family (Wife, son and myself) I pay $760 on a high deductible plan for health and $99 for dental for my wife and me. Once my son needs dental it'll most likely go up by about $40 for the dental. My only advice is to really sit down and determine what you're going to need for coverage and depending on that choose a high or low deductible. We started out on a low and realized we really would be better off on a high one so switched at the next enrollment. Good luck.