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So the initial discussion was from the employee's perspective. Frankly, I'd go for employee status. There's nothing preventing an employee from working from home at various odd hours. Plus employees are covered by unemployment insurance and Worker's Compensation (or State Industrial) insurance. Those are very significant benefits.

Dental insurance is generally a waste of money. Stick the $20 or $30 a month into a savings account instead, and brush and floss daily. Get cleanings twice a year that include a quick exam by the dentist (mine run about $80 a cleaning). Xrays every other year (maybe $100) to look for hidden problems.

As an employer, I wouldn't give an option. If you're on-site for 30 or more hours a week, you're an employee, not a contractor. If you don't do significant amounts of similar work for other businesses, you're an employee.

Trying to squeeze into an independent contractor situation generally isn't worth the effort.

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