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If you make more than $400 a year from self-employment (before expenses), you are required to file a tax return. If you are making 300/month, which is $3,600 you need to file even if you have 0 net profit (your expenses are more than your income).
Yes. IRS will not consider any relieve until you file all unfiled returns.
If you need help and don't want to pay fortune to CPA, you can use IRS services for free - taxpayer advocate services.
And here's contact for Oregon office in Portland: https://www.irs.gov/Advocate/Local-Taxpayer-Advocate#Oregon
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