Thank you so much for pointing this out! I didn't even consider wash sales. Looking at my trading pattern, I definitely bought back into some positions within that 30-day window after selling at a loss. Does the wash sale rule apply across different brokerage accounts too? Like if I sell at a loss on Fidelity and then buy the same stock on Robinhood within 30 days?

Yes, the wash sale rule absolutely applies across different brokerage accounts. The IRS doesn't care which platform you use - if you sell at a loss on Fidelity and buy the same stock on Robinhood within that 30-day window, it's still a wash sale. This is actually one of the biggest traps for traders who use multiple platforms. Your individual brokers won't know about trades you make elsewhere, so their reporting might not flag wash sales that actually exist when you look at all your accounts together. This is why tax software that can consolidate all your trading activity is valuable - it can identify wash sales that individual brokers miss.

How much trading do you have to do to qualify as a "trader" vs just an "investor"? I probably make like 5-10 trades a week, not sure if that's enough.

Does this still apply if you're a w2 employee but work remote? My company is based in another state but I work from home 100% of the time.

Unfortunately, if you're a W2 employee working remotely, you currently can't take the home office deduction, even if you work from home 100% of the time. The Tax Cuts and Jobs Act suspended home office deductions for employees through 2025. This deduction now only applies to self-employed individuals, independent contractors, or other business owners. If you get a W2 from your employer, you can't claim it regardless of your remote work status. Some companies offer stipends for home office expenses instead, so it might be worth asking your HR department if that's an option.

But wouldn't I save more using the regular method with my specific expenses? The simplified method seems like it would give me a much smaller deduction given the high housing costs in my area.

Thanks for this suggestion! So if I understand right, I could open this SEP IRA now and put some money in it before filing, and that would lower my taxable income? How is this different from a regular IRA? And can I still do this even though we're already in 2025?

Yes, that's exactly right. You can open and fund a SEP IRA for 2024 all the way up until the tax filing deadline (April 15, 2025), including extensions if you file for one. The main difference from a regular IRA is the contribution limit. A traditional IRA only allows you to contribute $7,000 for 2024 (or $8,000 if you're 50+). A SEP IRA lets you contribute up to 25% of your net self-employment income or $69,000, whichever is less. So if you made significant 1099 income, you can potentially shelter a lot more money from taxes.

What apps do you recommend for tracking expenses? I'm terrible at keeping receipts and always forget what things were for by tax time.

Wait, I didn't know rental income could qualify for QBI. Does my rental automatically count as a business, or do I need to do something specific to qualify? Is there a minimum number of hours I need to spend managing it?

Rental property doesn't automatically qualify for QBI. The IRS has a "safe harbor" rule that requires you to maintain separate books and records for each property, spend at least 250 hours per year on rental activities (property management time counts), and keep contemporaneous records of time, dates, and services performed. If you use a property management company, you'll need to carefully document any additional time you spend on rental activities. Another option is to qualify as a "real estate professional" for tax purposes, but that requires 750+ hours annually in real estate activities. If your property doesn't meet the safe harbor requirements, you might still qualify under general business principles, but that gets more complicated.

Would repairs done before renting out the property count as startup expenses or improvements? I'm about to rent my house and need to fix some things first.

That's really interesting about the Cash Balance Plan - I've never heard of that before. Is there a specific income threshold where it makes sense to set one up? And is it something that can be established quickly before year-end?

Cash Balance Plans generally make the most sense when your income is consistently over $300,000, though the benefits increase substantially at higher income levels. They're especially valuable for business owners in their 40s or 50s who need to catch up on retirement savings. Setting one up requires some lead time - typically 2-3 months for the plan design and legal documentation. While it's getting tight for this tax year, it's still possible if he acts immediately. The contribution deadline would be the business tax filing deadline (including extensions), but the plan must be established before year-end to count for this tax year.

The home deduction suggestion seems risky. I tried that a few years ago and got audited. The IRS is super picky about what qualifies as a legitimate home office deduction.