Your work plan sounds pretty cheap actually. Get all the details on it and compare it to what’s out there (many places will give you free quotes and details on their plans). Don’t get fooled by places throwing low numbers out there in ads, they’re often quoting very stripped down versions that have insane deductibles and crap coverage.

When I lived in Ma (about 6 years ago) I was paying over $800/mo for family coverage as being self employed. We were in great health, non-smokers and 1 child.