I hadn't thought about splitting the services like that! Do you find that the bookkeeper is knowledgeable enough about tax matters to help you categorize expenses properly? And how did you find a good virtual bookkeeper?

My bookkeeper is definitely knowledgeable about proper expense categorization for tax purposes - that's actually one of the main benefits. She ensures everything is tagged correctly throughout the year so tax filing is much simpler. She also helps identify potential deductions I might have missed. I found my virtual bookkeeper through the QuickBooks ProAdvisor directory. Look for someone who has experience specifically with rental properties and small businesses. I interviewed three before choosing one, asking specific questions about their familiarity with Schedule E, home office deductions, and vehicle expense tracking. The right bookkeeper can save you money not just on CPA fees but on taxes too by keeping meticulous records.

How did you find out they weren't actually licensed? Is there a way to verify CPA credentials before hiring someone?

1 I didn't even think about that. My shares were just in a regular account through the employee program, not in any tax-sheltered account. I wish I had put them in a TFSA now! Would have saved me a bunch on taxes. Is it too late to do anything about the tax situation now that I've already sold?

21 Unfortunately, once you've sold the shares outside of a registered account, you can't retroactively shelter them from tax. The capital gains tax will apply as others have explained. For future reference though, you might want to consider using your TFSA contribution room for any new investments. The annual TFSA contribution limit for 2025 is $7,000, and if you haven't used your room from previous years, you might have quite a bit of contribution space available. Any investments you hold in a TFSA can grow and be sold tax-free.

8 That calculation seems about right based on average tax rates. Important to note that if this pushes OP into a higher tax bracket, a portion could be taxed at a higher rate. Also don't forget that if there were any dividends received while holding the shares, those would have been taxable in the years they were received!

Thanks for mentioning this! Do you know if there's a minimum amount I need to earn from Doordash before I have to worry about quarterly payments? I might not do as much delivery work next semester when my classes get harder.

The quarterly payment requirement is based on your total tax situation, not just how much you earn from Doordash. The general rule is if you expect to owe $1,000 or more in taxes when you file your return, you should make estimated payments. If you think you'll make less next semester, you can adjust your estimates accordingly. The 1040-ES form helps you calculate this based on your projected income. Another option is to increase the withholding at your pizza job to cover the taxes on your Doordash income - you can do this by submitting a new W-4 form asking for additional withholding.

Just be careful with deductions. My brother tried to claim his entire phone bill and got audited. The IRS made him prove what percentage was actually for Doordash vs personal use. Better to be conservative and keep good records!

That's a really good point. I just checked my student portal and it looks like they did exactly that! Even though I paid in January 2022, they've categorized it as Fall 2021 payment (even though it was for Spring 2022 classes). Is that correct accounting? Can I still claim it for 2022 since that's when I actually paid it?

For education credits, what matters is when you made the payment, not how the school categorized it internally. If you have proof (bank statement, credit card statement, etc.) showing you paid in January 2022, you can claim it on your 2022 taxes regardless of how the school categorized it. The IRS specifically states that qualified education expenses are claimed in the year they're paid, not necessarily the year the education occurs. So if you paid in 2022, those are 2022 expenses for tax purposes. The 1098-T is just informational - you're responsible for reporting the correct amounts based on when you actually paid.

Is that actually legal though? Entering different numbers than what's on your official tax forms sounds risky. Couldn't that trigger an audit?

Thanks for bringing that up! What kind of documentation would be acceptable for proving the value? The property was last assessed about 3 years ago for tax purposes in the foreign country. Would that old assessment work or do I need something more recent?

The foreign tax assessment from 3 years ago is a good starting point, but ideally you want something more current. The IRS is looking for a reasonable basis for the reported value at the time of the gift. If property values have changed significantly in that area over 3 years, the old assessment might not be accurate. If getting a new formal appraisal isn't practical before the deadline, you could include the tax assessment along with documentation of comparable property sales in the same area from around the time you received the gift. Real estate listings or sales data for similar properties can help establish current market value. Just include a brief statement explaining your valuation methodology.

If you've already filed your tax return, you'll need to send Form 3520 separately. Make sure to include a copy of your filed tax return with it so the IRS can match them up. But don't file an amended return just for this - Form 3520 is filed separately even though it's due on the same date as your regular return.