Doesn't the IRS charge penalties if you don't withhold enough through payroll though? I thought there was some rule about having to withhold 90% of what you'll owe?

The IRS has a "safe harbor" rule - you won't face penalties as long as your withholding plus estimated payments total either 90% of your current year tax or 100% of last year's tax (110% if your income is over $150k). Quarterly estimated payments count the same as withholding for meeting these requirements. The only real difference is you have to be disciplined enough to set aside the money and make the payments yourself, rather than having it automatically taken from your paycheck.

This is actually not great financial advice. Intentionally overwithholding means you're giving the government an interest-free loan all year. Better to get your withholding right and invest the difference.

Great suggestion about the library - didn't think of that! Did you find a particular order of topics helpful when you were learning? I'm wondering if I should start with income, then deductions, then credits, etc., or if there's a better learning path.

I found it most helpful to start with the basics of filing status and income recognition, then move to adjustments to income (above-the-line deductions), then standard vs. itemized deductions, and finally credits. This follows the flow of a 1040 form which helped me understand how everything connects. After mastering individual returns, I branched out to self-employment, investments, and rental property. The key is building from simple to complex - master W-2 employee returns before tackling Schedule C business income or Schedule E rental property.

This is so true. I've learned more from TaxSlayer's help bubbles than I did in an intro to taxation class I took. Plus you can try different scenarios and see how they affect the outcome immediately.

This is super helpful. My uncle just sent the money through Venmo with a note saying "for your photography business - good luck!" Would a screenshot of that be enough documentation? Or should I ask him for something more formal?

A screenshot of the Venmo transaction with the note is actually perfect documentation! Save it as a PDF and keep it with your tax records. That clearly shows both the amount and the gift intent, which is exactly what you'd need if questioned. The key is having something that shows it was a gift rather than payment for services. That Venmo note makes it clear, so you're good to go. No need for anything more formal unless you want it for extra peace of mind.

You'd depreciate normally! The source of funds doesn't affect depreciation rules at all. I'm a photographer too and had a similar situation when I bought a $3000 lens with gift money. You'd depreciate it over its useful life (usually 5 years for photography equipment) or you might qualify for Section 179 deduction to expense it all in the first year.

Does this mean if I won $10k at a casino but lost $12k overall, and I take the standard deduction, I'm basically paying taxes on $10k I didn't actually make? That seems totally unfair!

Exactly right. If you won $10k but lost $12k overall, you still have to report that $10k as income. If you take the standard deduction, you don't get to deduct any of your losses. This is why gambling taxation is particularly harsh. You're effectively paying taxes on money you didn't get to keep. It's one of those tax code quirks that disproportionately affects average people rather than professional gamblers who typically have enough deductions to itemize anyway.

I'm curious - did you have W-2Gs for your winnings? I've heard the IRS automatically gets those from casinos so they know exactly what you won, but have no way to verify losses without documentation.

But what if I literally have zero income for 2024? Can I still file and claim these credits? My child was just born a month ago, and I'm still waiting on disability approval.

You can still file taxes with zero income, and you absolutely should if you have a dependent child. The Earned Income Credit has special rules that might apply even with zero earnings in your situation. For the Child Tax Credit, up to $1,600 per child is refundable (called the Additional Child Tax Credit), meaning you can receive it even if you have no tax liability. Since your child was born this year, they count as your dependent for the entire 2024 tax year.

That's actually a really important point I hadn't considered. I'm applying for several assistance programs right now while waiting on disability approval. I definitely don't want to mess up those applications.

I'm glad you brought that up. Each program has different rules, but many require you to report if you're being claimed as a dependent on someone else's taxes. This could potentially: - Change your household size calculation for benefits - Affect income limits since they might count some of your brother's income - Impact housing assistance eligibility or priority I'd recommend contacting the specific programs you're applying for and asking directly how being claimed as a tax dependent would affect your application. It's much better to know beforehand than to have benefits reduced unexpectedly.