Has anyone used TurboTax to handle this kind of situation? I'm wondering if there's a way to note in the software that you're still waiting on the official receipt.

Just wanted to add my experience here - I went through something very similar last year with a $500 donation where the charity never responded to my requests for an official receipt. I ended up consulting with a tax preparer who told me that while the PayPal receipt alone isn't technically sufficient for amounts over $250, the IRS does consider your good faith efforts to obtain proper documentation. What really helped my case was keeping a detailed record of every attempt I made to contact the charity - screenshots of emails sent, phone call logs, even trying to reach them through their website contact form. I also verified the charity's 501(c)(3) status on the IRS Tax Exempt Organization Search tool and printed that out as supporting documentation. In the end, I claimed the deduction with the documentation I had, and fortunately was never questioned about it. But having that paper trail of attempting to get the proper receipt gave me peace of mind. The key is showing you made reasonable efforts to comply with the documentation requirements, even if the charity was unresponsive.

Random question from an accountant's wife: has anyone here calculated if it's actually cheaper to pay a Canadian accountant and a US accountant separately, or find one of those specialized cross-border accountants that do both returns?

As someone who's been navigating dual US-Canadian taxation for about 3 years now, I can confirm that while it's complex, it's definitely manageable once you understand the basics. A few key points that might help: 1. You'll almost certainly end up paying less in total taxes than you think. Canadian taxes are generally higher, so the foreign tax credits usually eliminate most US federal tax liability. 2. Don't forget about provincial taxes in Canada - they vary significantly by province and aren't covered under the treaty the same way federal taxes are. 3. If your employer offers stock options or RSUs, get professional advice ASAP. The timing of taxation between the two countries can create some really tricky situations. 4. Consider opening your Canadian accounts before you actually move - some banks are more willing to work with US persons if you establish the relationship while still in the US. The first year is definitely the hardest as you figure everything out, but it gets much more routine after that. Just budget for good professional help at least for the first filing to make sure you're set up correctly!

Important thing to know - if you're expecting refunds, you only have 3 years from the original filing deadline to claim them. So for example, 2020 refunds can still be claimed until April 2024, but anything before that is gone forever if you were owed money. BUT if you owe the IRS money, there's no time limit on when they can come after you. So definitely better to address this proactively like you're doing now!

I went through something very similar about 3 years ago - hadn't filed for 6 years due to a combination of job changes, a messy divorce, and just pure avoidance anxiety. The longer I waited, the more terrifying it seemed. Here's what worked for me: Start by getting your Account Transcript from the IRS online (irs.gov). This will show you if they've already filed substitute returns for you (which they sometimes do if you have W-2 income). If they have, you'll see exactly what they think you owe. Don't try to tackle all years at once - it's overwhelming. I started with the most recent year and worked backwards. Focus on getting accurate numbers rather than rushing through everything. One thing that really helped my anxiety was realizing that the IRS actually wants to work with you once you make contact. They have payment plans, penalty abatement options, and they're generally reasonable if you're making a good faith effort to comply. The relief of finally addressing it is incredible. Yes, there will be some penalties and interest, but it's probably not as catastrophic as your anxiety is telling you it will be. You've got this!

22 Has anyone used TurboTax to handle reporting this kind of situation? I'm in a similar situation with medical crowdfunding and wondering if the basic version handles this or if I need to upgrade.

I went through something very similar after my car accident last year. My family set up a GoFundMe that raised about $28,000 for my medical expenses, and I was terrified about the tax implications. After consulting with a tax professional, I learned that medical crowdfunding donations are indeed treated as gifts and aren't taxable income to you as the recipient. The key is that people donated without expecting anything in return - they were helping with your medical crisis out of generosity. A few important points from my experience: - Keep detailed records of the GoFundMe campaign, including the total raised and donor information - Save all your medical bills and receipts showing how the money was used - If you itemize deductions, you can only deduct medical expenses you paid out of your own pocket (not the portion covered by GoFundMe) - The donors are responsible for any gift tax reporting if they gave over the annual exclusion limit I kept a simple spreadsheet tracking donations received vs. medical expenses paid, which gave me peace of mind. You're not required to report the gifts as income, but having good documentation is always smart. Hope this helps ease your worry!

One more thing to consider - state taxes! I found out that while my settlement wasn't taxable federally, my state had different rules. Double check your specific state's treatment of personal injury settlements.

Hey Chloe! I went through something similar a few years ago after a slip and fall accident. You're absolutely right to be cautious about the tax implications - it's smart to get this figured out before you spend any of the money. From my experience and what I learned, personal injury settlements for physical injuries are generally NOT taxable at the federal level. Since you mentioned this was from being hit by a car while walking (clearly a physical injury situation), the portion of your settlement compensating you for medical bills, pain and suffering, and physical injuries should be tax-free. However, keep an eye out for any parts of your settlement that might be taxable: - Any interest earned on the settlement amount - Compensation specifically for lost wages/income - Punitive damages (if any) - If you previously deducted medical expenses related to this accident on past tax returns and are now being reimbursed My advice would be to get a detailed breakdown of your settlement from your attorney showing how the money is allocated across different categories. This will make it much easier to determine what (if anything) needs to be reported as taxable income. Also don't forget about potential health insurance subrogation - if your health insurance paid for any of your medical treatment, they might have a claim against your settlement. It won't affect the tax treatment, but it could reduce what you actually keep. Hope this helps and congrats on getting through what I'm sure was a stressful situation!