What are the things that I need to know when I’m doing freelancing/work for hire under F1-OPT? Am I going to involve anything tax-related even when my US presence is under 5 years? What is it for me to fill up the W-9 and 1099-MISC forms?

The earnings within a geography have an immediate tax consequence – whwther the person will be physically present “under 5 years” means absolutely nothing.
Be sure that IRS will take its share.

If you have an exemption from the IRS about that “under 5 years” rule, please share it as it will be the first one of its kind.

The part about this not working should’ve been put first, but I suppose you already know that answer: working for hire (freelancing or on payroll) is not permitted for F-1 visa holders.
Why?
That’s because the application for
student visa stated – and you had signed it under the penalty of perjury – that you will not seek employment while in US as you have sufficient funds for your tuition and room/board. Not you, all – each and every – foreign student signs this same statement.

Once you turn around and make income, well, you can wave goodbye to your visa and your stay in US.

Even if you do it differently, and let’s say, you are only receiving income from someone else’s work – it will be treated the same way.
No, you won’t fill out W-9 and 1099 form – the reporting on your income will be for your records with copy of it going to the IRS directly.
Why?
That’s the law.

Only when you specifically demand that the work is paid for 100% under the table with no records, then the employer will take advantage of you by underpaying you (severely).
Small employers
can do it; and big employers (who have a lot to lose if they mess with the IRS) won’t do it at all – it’s not worth it for them.

How do you know which employer is which?
If you’re asked about W-9 form, it will ask abotu the SSN, and once that is out of your hands, your income will go to the IRS directly. Again, it’s the law, it’s how US works.
1099 form is the record which will be given to you and which will you have to explain once you’re asked about your
student status (F1 visa is not a work authorization).

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