Thanks so much for this reassurance! I'm still a bit nervous about taking the deduction without photos. For the documentation you mentioned - would a detailed written description with measurements and a hand-drawn floor plan be sufficient? Or should I try to find other proof like emails sent from that workspace?

A detailed written description with measurements and a hand-drawn floor plan is absolutely sufficient documentation. Date it and keep it with your tax records. Including details about the built-in desk, the three walls forming the alcove, and how you used the space for specific business activities strengthens your case. Adding some supporting evidence like business emails, client invoices you created there, or phone records showing client calls would be helpful supplementary documentation, but not strictly necessary. The IRS understands that people move and may not have photographs of previous spaces. Your contemporaneous written records are considered valid documentation, especially when they're detailed and consistent with your business activities.

TurboTax Self-Employed version handles home office deductions pretty well. It walks you through all the questions and helps calculate both the regular and simplified methods. I've used it for the past 3 years with no problems. Just make sure you get the Self-Employed version, not the regular one.

3 Wait, is that really true even if you're claimed as a dependent? I thought dependents couldn't open retirement accounts.

9 Yes, it's absolutely true! Being claimed as a dependent doesn't affect your ability to contribute to a Roth IRA. The only requirements are that you have earned income and don't exceed the contribution limits (either your total earned income or $6,500 for 2023, whichever is lower). Many parents miss this opportunity for their working teens. It's a fantastic way to start building tax-free retirement savings early, and the compound interest over decades is incredible. I opened mine at Vanguard with help from my parents when I was still in high school.

11 Good point! Does anyone know if you need to file state taxes if you're under 18? I'm in California and making about $8,000 this year through my parent's Venmo.

Which state are you in? I'm in NJ and now I'm worried about this.

I'm in Massachusetts. Each state has their own rules - I believe in NJ you can deduct gambling losses but only against gambling winnings, similar to federal. But always check with your state's department of revenue to be certain, as these rules change occasionally, especially with the expansion of legal online betting. Massachusetts doesn't allow gambling loss deductions at all on the state return, which means you pay state tax on all your winnings regardless of losses. Several other states have similar limitations.

Thanks for bringing this up! I haven't received any W-2G forms yet, but I did have a few big wins that were well over $600. Do you know if the betting sites report this information to the IRS directly? I'm wondering if they'll know about my winnings even if I don't report them (though I plan to report everything properly).

Yes, the betting platforms do report those large winnings to the IRS using your SSN, so the IRS will know about them regardless of whether you receive a W-2G or not. The platforms are required to report certain large wins, and some will automatically withhold taxes on major payouts. If you don't report winnings that were reported to the IRS, you'll almost certainly get a notice from them later. That's why it's crucial to keep good records of both wins AND losses throughout the year, so you can properly document everything if needed.

Thank you so much! This breakdown is super helpful. Quick follow-up though - for the actual amount of withholding, should I be using what was initially withheld ($78k) or the net amount after they already got that partial refund through the T2062 process?

You should use the net amount after the partial refund. So if $78k was initially withheld but $22k was already refunded based on the T2062 adjustment, you'd report $56k on line 43700 as the withholding tax amount. The CRA system should already have a record of both the initial withholding and the T2062 adjustment, but I always recommend including a brief note with the return explaining these amounts to avoid any confusion during processing.

For non-residents, you don't need to file a separate provincial tax return. The federal T1-NR handles both federal and provincial taxation. Non-residents pay a flat 25% federal tax on taxable Canadian property, with no separate provincial component. Just make sure you're correctly identifying the property's location on the return since this affects CRA's internal processing, but you won't need to complete any provincial-specific forms for a non-resident property sale.

If you put zeros in Parts 1 and 2, do you need to do any calculations or just literally put 0 in each box? And have you ever been audited or questioned about your Roth withdrawals?

You just put a zero in each box, no calculations needed for parts that don't apply to your situation. It's just to show you didn't accidentally skip that section. I've never been audited specifically about my Roth IRA withdrawals. I did get a general review letter once about three years ago, but it was about something completely different (they questioned some business deductions). My Roth withdrawal reporting with the zeros-not-blanks approach has never been flagged in the 12 years I've been doing it this way.

In my experience, let the software do its thing. TurboTax is programmed to complete forms correctly based on your inputs. If it's filling parts 1 and 2, it's probably putting zeros or calculating something based on your overall tax situation that might be relevant. Tax software is designed to handle these nuances.