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Real estate agent. Using your previous year to estimate works too. Having last years also will give you a total of expenses to average in. You could send bare minimum in, and then lay off at the end just make sure you have the money. I've also never known anyone to get fined but they doesn't mean it doesn't happen. Now if you want to get into the fun loop holes you can open an S-Corp that files its own returns. Then you can open an LLC under the Corp for your landscaping business and funnel money up to the Corp to avoid heavy income taxes on your 1099. You can also use an LLC for individual projects. Let's say you want to build and sell a home, open an LLC for any.

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