Just be careful! A friend of mine tried to deduct the difference between flying and driving for a similar situation, and it triggered an audit. The IRS disallowed the deduction because they determined the primary purpose of the trip was personal (family event). They said personal trips with some business activities don't qualify for travel deductions.

The key distinction here is that you're not just adding some business activities to a personal trip - you're being forced to change your entire travel method specifically because of business equipment requirements. This creates a stronger case for deducting the incremental costs. I'd recommend documenting everything thoroughly: get quotes for what flights would have cost, keep all driving-related receipts (gas, hotels, meals during travel), and most importantly, document why the equipment was essential and couldn't be shipped or transported any other way. Client emails or contracts showing the equipment requirements would be valuable supporting evidence. One thing to consider is whether you could potentially ship the equipment separately and still fly yourself. If shipping isn't viable due to timing, fragility, or cost, make sure to document why. This helps establish that driving was truly the only reasonable business option, not just a preference. The IRS generally allows deductions for additional costs incurred solely due to business necessity, but they'll want to see clear evidence that the extra expense was unavoidable for legitimate business reasons.

Just adding another data point - I'm from Montreal and I used the US Consulate route last summer. Made an appointment online, brought my passport + W-7 + tax return, and they certified the copy right there. Took about 25 minutes total. Mailed everything to the IRS and had my ITIN in about 7 weeks. One tip they gave me at the consulate: make sure you call ahead to confirm they offer the passport certification service specifically for ITIN purposes. Some smaller consulates apparently don't offer it or have limited hours for this service.

Great thread with lots of helpful info! I went through this process as a Canadian in 2023 and wanted to add a few practical tips: 1. **Timing is everything** - If you're applying during tax season (January-April), expect longer processing times. I applied in May and got my ITIN in 6 weeks, but friends who applied in February waited 10+ weeks. 2. **Double-check your W-7 form** - The most common mistake I see other Canadians make is in Section 6a where you select your reason for needing an ITIN. Make sure you're checking the right exception box based on your specific situation. 3. **Keep copies of EVERYTHING** - The IRS will return your certified passport copy, but sometimes things get lost in the mail. I made photocopies of all documents before sending them. 4. **US Consulate appointment booking** - Book your consulate appointment ASAP. In Toronto especially, they can be booked weeks out. You can find the online booking system on the US Consulate website. The certified copy route is definitely the way to go - never send your original passport! I was traveling internationally while my application was processing and had zero issues.

I went through something similar with a travel giveaway from TikTok last year! The company kept giving me the runaround on the 1099 too. What really helped me was creating a detailed timeline of all my communications with them - dates, what they promised vs. what was delivered, screenshots of the original giveaway post, etc. Since they're already past the January 31st deadline for sending the 1099, I'd recommend sending them one final demand via certified mail with a clear deadline (maybe 10 business days). In that letter, specifically mention that you need the 1099-MISC for tax filing purposes and that they're already late on their legal obligation. Meanwhile, start gathering your own documentation for fair market value calculation. You mentioned having flight receipts which is perfect. For the accommodation, even though it was a personal home, research what similar properties would rent for in that area during your stay dates. The $250 gift card is straightforward to value. If they still don't respond, you can file your taxes reporting the actual value received as "Other Income" and keep all your documentation. The IRS is pretty understanding when taxpayers make good faith efforts to comply despite uncooperative prize sponsors. Just make sure your valuation is reasonable and well-documented!

What a frustrating situation! You're absolutely right to be concerned about this. Since you filled out a W-9 and the prize value likely exceeds $600, they should have sent you a 1099-MISC by January 31st - they're already well past that deadline. Here's my take: Document everything you actually received versus what was promised. You have the flight receipts (great!), the $250 gift card, and you stayed at their personal vacation home. The key is that you only owe taxes on the fair market value of what you actually received, not the inflated promotional value. For your tax filing, I'd calculate it like this: - Flight costs (you have receipts) - Fair market value of the vacation home stay (research comparable Airbnb/VRBO properties in that area for your dates) - $250 gift card value Send them one final certified letter demanding the 1099 with a specific deadline (maybe 10 business days). If they don't respond, proceed with reporting the actual fair market value as "Other Income" on your tax return. Keep all your documentation showing how you calculated the value. The IRS understands when prize sponsors are uncooperative, so as long as you make a good faith effort to determine reasonable fair market value and keep detailed records, you should be fine. Don't let their poor communication put you at risk for penalties!

I went through this exact situation when my mom's trust became irrevocable. The key thing to understand is that the trust's tax obligation exists regardless of whether you actually distribute the money or reinvest it. What helped me was getting a clear picture of the trust's "accounting income" versus "taxable income" - they're not always the same thing. The IRS looks at what the trust earned, not what you did with those earnings afterward. One strategy that worked for my situation was making small distributions to the beneficiaries (my siblings' kids) and having those funds go directly into 529 education savings accounts in their names. This way the income got taxed at their lower rates instead of the trust's compressed brackets, but the money was still being saved for their future benefit. You'd need to check if your trust document allows this kind of arrangement and whether it makes sense for your family's situation. Also, don't forget that the trust can deduct certain administrative expenses like trustee fees, accounting costs, and investment management fees. These deductions can help offset some of the tax burden.

This is a common confusion that many new trustees face! The key insight here is that irrevocable trusts are separate tax entities, so they owe taxes on income they retain regardless of whether that income is reinvested or sits in cash. The $2600 "distributed" amount you're seeing in TaxAct might be a software quirk or it could be related to how the program is calculating potential distributions under the trust's terms. I'd double-check your entries to make sure you haven't accidentally indicated any actual distributions. A few practical suggestions: 1. Consider consulting with a tax professional who specializes in trusts - the compressed tax brackets make this worth the investment 2. Review your trust document carefully to see if you have authority to make distributions now, as this could shift tax burden to your children at lower rates 3. Keep detailed records of all trust income and expenses, as the trust can deduct legitimate administrative costs Remember, as trustee you're responsible for ensuring the trust pays its taxes, but those taxes come from trust assets, not your personal funds. The trust should have its own bank account and tax ID number for this purpose.

Has anyone successfully deducted home office and tech equipment for their S-Corp trading business? My accountant says since trading isn't technically a "service" I provide to others, I might not qualify for these deductions even though I have a dedicated home office where I exclusively do my trading work.

One thing that might help clarify your situation is understanding the difference between "investment activity" and "trading business activity" within your S-Corp. The IRS looks at factors like frequency of trades, time spent, and intent to profit from short-term price movements versus long-term appreciation. If your S-Corp is engaged in trading as a business (not just investment), you can legitimately pay yourself a reasonable salary for managing those trading activities. The salary reduces the S-Corp's net income, and the remaining profits (still characterized as capital gains) flow through to your personal return. Regarding your question about reinvesting profits - this doesn't change your tax liability. You're taxed on realized gains whether you distribute the cash or reinvest it. However, if you're consistently profitable and reinvesting, you'll want to make sure you have enough cash flow to cover the taxes on the pass-through income. One important consideration: if you're making "multiple short-term trades" as you mentioned, you might want to explore whether your S-Corp qualifies for trader tax status and consider a Section 475 mark-to-market election. This could potentially be more advantageous than traditional capital gains treatment, especially if you experience volatile trading results.