I work in payroll - completely normal for this time of year. The SSA has to process millions of W2s before sending to IRS

Just wanted to add some context as someone who's been through this process multiple times - the timing can vary significantly depending on your employer's payroll provider. Large companies using systems like ADP or Paychex typically get their W-2s submitted faster, while smaller employers might take until closer to the January 31st deadline. Even after submission, the IRS wage transcript system updates in batches, not continuously. One thing that helped me last year was setting up IRS account alerts, but honestly checking every few days just made me more anxious. The transcript will populate when it's ready, and you'll have plenty of time to file accurately. If you're really pressed for time, you can always file using the W-2 your employer provides directly and the IRS will match it up later during processing.

Something I haven't seen mentioned yet is that you should check if your state has any maximum contribution limits for 529 plans. Most states have aggregate contribution limits between $300k-$500k per beneficiary. Also, think about who should own the 529 accounts. If grandparents own them, the distributions don't count as income to the student on the FAFSA. But if you own them, they're considered parental assets which have less impact on financial aid than student assets.

Given your substantial windfall and complex situation, I'd recommend a multi-pronged approach rather than putting all your tax optimization eggs in the 529 basket. Since 529 contributions don't reduce federal capital gains taxes (as mentioned earlier), consider these additional strategies: 1. **Installment sale structure** - If possible, restructure part of the business sale as an installment sale to spread the capital gains over multiple years, potentially keeping you in lower tax brackets. 2. **Charitable remainder trust** - If you're charitably inclined, this could provide immediate tax deductions while generating income for retirement. 3. **Opportunity Zone investments** - Depending on timing, rolling some gains into Opportunity Zone funds could defer and potentially reduce capital gains taxes. 4. **State tax planning** - Some states have no capital gains tax. Depending on your residency situation around the sale, this could be significant. For the 529s specifically, I'd suggest contributing enough to maximize any state tax deductions you're eligible for, but don't over-contribute given your kids' ages and remaining education costs. Your sophomore and younger two would benefit most from the tax-free growth. With 20 years until retirement and another liquidity event expected in 4-6 years, you have flexibility to optimize across multiple tax years rather than trying to minimize everything in this single year.

Has anyone used the IRS's Tax Withholding Estimator for this purpose? I'm doing solar next year too and tried using it, but got confused because it doesn't seem to have a specific input for planned tax credits like the Residential Energy Credit.

One thing I haven't seen mentioned yet is the timing of when you actually place your solar system in service. The credit is claimed in the tax year when the system is placed in service (when it's installed and operational), not when you make the purchase or sign the contract. So if you're planning installation for 2025, make sure to coordinate with your installer about the timing. If installation spans across December 2025 and January 2026, you'll want to clarify which year the system is considered "placed in service" for tax purposes. Also, keep all your documentation! You'll need receipts showing the total cost of the system, and if you're including battery storage, make sure those receipts clearly show the battery capacity meets the 3 kWh minimum requirement to qualify for the credit. The IRS has been pretty clear that they're scrutinizing these large credits more closely, so having organized documentation will save you headaches if you get selected for review.

I think most people here are missing an important point - have you checked if there's a tax treaty between the US and Canada that might apply to your situation? The US-Canada tax treaty has specific provisions about different types of income to prevent double taxation.

Just wanted to add another perspective here - you should also consider consulting with a tax professional who specializes in international tax matters, especially given the complexity of your situation with the Canadian settlement. While the general advice about reporting the settlement as taxable income is correct, there are some nuances that might apply to your specific case. For example, the timing of when you received the settlement versus when the legal case was resolved could affect which tax year you need to report it in. Also, if any portion of the settlement was specifically allocated to reimburse you for medical expenses you previously deducted, that portion might be taxable under the "tax benefit rule." Given the $43,000 amount involved, the cost of a consultation with a qualified tax professional would likely be worth it to ensure you're handling everything correctly and not missing any potential benefits or requirements. They can also help you understand the FBAR filing requirements that others have mentioned and make sure you're compliant with all the international reporting obligations.

Does anyone know if you can deduct expenses against T4A income? I drive Uber on weekends and got a T4A this year, but I paid for gas, car maintenance, etc.

I went through this exact same situation last year with a T4A from some freelance work. Yes, you absolutely must report it - the CRA already has a copy and their systems will automatically flag any discrepancies between what you file and what they received. The good news is that TurboTax makes it pretty straightforward. When you get to the income section, there's a specific area for T4A slips. Just enter the information exactly as it appears on your slip. Since you mentioned it's from a side gig, it's likely in box 048 (self-employment income), which means you might also be able to claim some business expenses against it if you have any. Don't stress too much about owing extra tax - $2,800 isn't a huge amount, and depending on your tax bracket, the additional tax might be less than you think. Plus, if you have any expenses related to that side gig (equipment, supplies, portion of home office, etc.), those can help reduce what you owe. The key thing is just to report it honestly. The CRA is pretty reasonable when people are upfront about their income - it's when they try to hide things that you run into real problems.