Solo owner
You're an individual buyer with the self-employed deduction. Price both markets.
You plus one
A spouse on payroll or one W-2 employee opens guaranteed-issue small-group coverage. Often the answer when one person has a condition.
3–50 employees
Level-funded and traditional group plans, deductible to the business. Under 50 there's no mandate to offer coverage. Massachusetts is one of the most tightly regulated individual markets in the country: the state mandate requires coverage that meets minimum creditable coverage rules, and many non-ACA plans don't. Private options here are narrower than in most states, so the honest answer is usually a careful comparison, not a promise of savings.