As it pertains to employment law, we have a kind of complicated arrangement with one contractor. 1) She rents a house on the farm from the farm business. 2) She babysits for us as a household employee and will receive a W2 – we pay payroll taxes, she is covered by worker’s comp, and we pay state unemployment insurance; 3) She signed an independent contractor agreement with the property management LLC – for this, she cleans facilities for agritourism on a per unit basis – e.g., she gets $10 per booking for cleaning and sanitizing the bathroom and tidying a hipcamp site and she gets $50 for cleaning and sanitizing the airbnb suite according to the cleaning protocol, etc. – she has her own equipment like a vacuum but the business does supply cleaning supplies like sanitizer – she used to clean professionally but doesn’t currently clean for anyone else – and she decides which jobs she wants to do and I will do the rest; she submits invoices when she wants to get paid; 4) She signed an independent contractor agreement with the non-profit LLC that operates the farm – she was working on another farm before she volunteered with us through WWOOF and decided to stay at the end of the season. Before our previous independent contractor decided to devote more time to her own farm while pursuing a career in nursing she oriented our current contractor to the farm tasks and together they opened and managed the farm stand, planned, designed and implemented the produce operation utilizing our hoop house and intensive annual beds and they both proficiently ran the farm independently with only minimal input with regard to signing off on the final design of the intensive beds and some spreadsheets I created for accounting purposes to track farm stand sales, etc. She has a number of her own tools, she also utilizes our personal tools (which are not owned by the farm business); she also has worked several times on another farm – helping to plant trees; she propagated seed starts on her own and sold them to the farm; she makes her own firewood bundles and sells them to the farm and to our household; she grew her own produce and sold it to the farm for resale at the on farm market; She operates independently and figures out the details about how to plan, propagate, plant, tend, harvest, sell a number of her own products and helps the farm augment it’s own operations. She independently cares for the sheep, goats and chickens. She is usually the one interfacing with veterinarians and other professionals when their services are needed. She also processes eggs for sale and she and I developed a egg processing and packing protocol that we both follow when we process and pack the eggs and recently revised together. When I’ve discussed this with a couple of independent accountants, they had no qualms about her being a 1099. But after reading the article, I am wondering if this is the best approach. Would it be less risky to just make her an employee of all of the businesses in addition to the household. Would it be possible for her to still independently create her own farm products and invoice us for the sale of those products, etc? To what degree does the fact that she is renting a house from us factor in to this equation? Any other recommendations about how to navigate this tricky arrangement?