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Yes, you need to file a tax return. If you had even $400 of self-employment income you are required to file a tax return. You will prepare a Schedule C for your business expenses.
All of your income including the bartending income and realtor income goes on that same tax return.
You have self-employment income for which you will pay self-employment tax for Social Security and Medicare. You will need to use online Premium software or any version of the CD/download so that you can prepare a Schedule C for your business expenses.
https://ttlc.intuit.com/questions/2926899-how-does-my-side-job-affect-my-taxes
https://ttlc.intuit.com/community/self-employed/help/what-is-the-self-employment-tax/00/25922
https://ttlc.intuit.com/questions/2902389-why-am-i-paying-self-employment-tax
https://ttlc.intuit.com/questions/1901340-where-do-i-enter-schedule-c
https://ttlc.intuit.com/questions/3398950-what-self-employed-expenses-can-i-deduct
https://blog.turbotax.intuit.com/self-employed/self-employed-tax-deductions-
calculator-2021-2022-50907/https://ttlc.intuit.com/questions/1901110-do-i-need-to-make-estimated-tax-payments-to-the-irs
https://turbotax.intuit.com/tax-tools/calculators/self-employed/
Or—-Use this IRS site for other ways to file for free. There are 8 free software versions available from the IRS Free File site
https://apps.irs.gov/app/freeFile/
Yes, you are supposed to file one return each year that includes all of your income.
I assume you got a 1099-NEC for your real estate work. If that's the case, you need to enter that along with your W-2 from your other job.
Here's how to get started on that:
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