Thanks for mentioning this! I actually did do some freelance work last year that I reported on Schedule C. Would I need to open a specific type of account for this SEP IRA thing? And does the contribution have to be from the freelance income specifically or can it come from my savings?

You'll need to open a specific SEP IRA account at a brokerage like Vanguard, Fidelity, or Schwab. Most have simple online applications and you can designate it as a SEP IRA during the account creation process. The contribution can come from any of your personal funds - it doesn't have to be directly from your freelance earnings. The important thing is that your contribution can't exceed 25% of your net self-employment income (after deducting expenses and the self-employment tax deduction). If you made $10,000 in net profit from freelancing, you could contribute up to about $2,500 to a SEP IRA which would directly reduce your AGI by that amount.

Qualified Charitable Distributions (QCDs) only work if you're 70.5 years or older, and they're made directly from your IRA to the charity. They don't technically reduce your AGI but they do reduce your taxable income. If you're younger, regular charitable contributions won't reduce AGI either - they're itemized deductions that come after AGI is calculated.

Can you explain more about tax loss harvesting? I've heard the term but don't really understand how it works or if it's something I should be doing.

Tax loss harvesting is basically strategically selling investments that have decreased in value to offset capital gains from other investments. For example, if you have stocks that have gained $5,000 and others that have lost $5,000, you could sell both and effectively pay no tax on the gains. You can also use up to $3,000 of net capital losses to offset ordinary income each year. Any unused losses above $3,000 can be carried forward to future tax years. It's a way to make your investment losses work for you by reducing your tax bill. Just be careful of wash sale rules - you can't buy substantially identical securities within 30 days before or after selling at a loss.

I used TurboTax and it handled the negative values correctly. The software automatically pulls the right numbers from Schedule D to the Qualified Dividends worksheet. You can click on the line items to see where the numbers are coming from if you want to double-check.

Does this mean I should always double check if software is making the right choice between standard and itemized? I've just been accepting whatever the software recommends.

Yes, you should always verify which deduction method is better for your situation. Most software will choose correctly, but understanding why is important. The standard deduction is simple - a fixed amount based on filing status. Itemized deductions add up your qualifying expenses (state/local taxes up to $10K, mortgage interest, charitable donations, certain medical expenses, etc.). If itemized > standard, use itemized. If not, use standard. Both programs will ultimately pick the higher option, but they differ in how clearly they show you the "losing" calculation.

I used Cash App Taxes last year and liked it, but it doesn't support some forms I need this year like K-1s from partnerships. For simple returns it's great tho.

Thanks for the heads up about Form 8283! Would I need to attach any documentation about the original price when I file, or just keep that information in case of an audit? And do you know if I need the charity to fill out part of the form?

You don't need to attach the original price documentation when you file - just keep all that info in your records in case of an audit. The IRS recommends keeping tax documentation for at least 3 years after filing. Yes, the charity needs to complete Part IV of Section A on Form 8283 to acknowledge receipt of the donated property. Make sure to get this filled out when you drop off the item or shortly after. They'll need to include their name, EIN, signature of an authorized official, and date of the donation. Some charities are familiar with this requirement, but smaller ones might need you to explain what you need.

Good point about itemizing! I made this mistake last year - went through all the trouble of documenting donations and then realized it didn't matter because we took the standard deduction anyway. Such a waste of time!

Does TurboTax automatically figure this out if you enter both types of contributions? Or do you have to manually separate them somehow?

TurboTax will ask you to enter both types separately. When you enter your W-2, it captures the code W contributions automatically. Then it will specifically ask if you made any additional contributions directly to your HSA outside of payroll. Just make sure you don't double-count by entering your payroll deductions again in the "direct contributions" section. Only enter any additional contributions you made separately from your paycheck.

That's a good point. How can you tell which portion came from the employer vs your own money if they're combined under the same code?