As an independent contractor, you are self-employed and are considered by the IRS as operating a small business doing what you doing such as an Artist
You can use TurboTax Home & Business to file your tax return.
Read this article for more information on filing as a Self-employed contractor Reporting Self-Employment Business Income and Deductions
How do I calculate the amount I should save from my income to actually afford to pay taxes, and how would I know if I'm included in this bunch who have to pay 4 times a year?
See this article on How to Determine What to Pay and When Estimated taxes
Use this Estimated tax calculator calculator
So, my last question is would I be required to report my art commission income as well-- if so how would I report it?
You would report this as Other Income and not as apart of your self-employed independent contractor income.
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