Thanks for the detailed list! I didn't realize payment processing fees were deductible - that's actually a significant amount for my business. Is there a good rule of thumb for determining what percentage of my internet and phone to deduct? I use both for business but obviously personal use too.

For internet and phone, you need to determine a reasonable business-use percentage. If you use your cell phone 70% for business and 30% personal, you can deduct 70% of those costs. Just make sure you can justify the percentage if asked. For payment processing fees, absolutely deduct them all! Those PayPal/Stripe/credit card fees add up quickly and are 100% legitimate business expenses. Don't forget the monthly fees plus the per-transaction percentages. Many new business owners miss these, but they can easily add up to thousands of dollars in deductions over a year.

I second this. Using a tax professional my first 2 years taught me how to properly do my taxes. Now I use TurboTax but actually understand what I'm doing. The education alone was worth the fee, and they likely will save you more than their cost.

Thank you for this explanation! I just checked and it looks like they ARE filing something called an 1120-S now instead of the Schedule C. So does this mean we're actually making the same amount of money but it just looks different on paper? Could this hurt my chances for need-based scholarships?

Yes, that's exactly what's happening! With an S-Corporation (Form 1120-S), the income gets reported differently even if the actual money coming in is the same. The business income flows through to your parents' personal return on Schedule E rather than Schedule C. This could definitely impact your need-based scholarships because the FAFSA and many scholarship programs look at adjusted gross income. With an S-Corp structure, sometimes more of the business income flows to the personal return because expenses get handled differently. Your parents should talk to their tax preparer about optimizing their S-Corp approach for both tax savings and financial aid purposes. There are legitimate strategies to properly categorize business expenses on the 1120-S that might help reduce the reported income while still following tax laws correctly.

This is actually a really good point. When I switched my restaurant to an LLC, we had to change how we tracked inventory and it made our first year look WAY more profitable than it actually was because of timing differences. It evened out the next year.

Does this actually work with mortgage lenders though? Don't they usually look at 2 years of tax returns? I wonder if they'd notice the pattern and question it.

It can work depending on the lender and your specific situation. You're right that they typically look at 2 years, but many put more emphasis on the most recent year, especially if your income is trending upward. The key is to be strategic and consistent. Don't make it look like you're manipulating numbers - instead, make legitimate business decisions about when to make major purchases or when to defer income. For example, delaying some business purchases until after you close on the home is completely legitimate. Lenders understand that self-employed income fluctuates naturally.

This is a really good point. When I did this last year, I was surprised how much extra I ended up paying because I forgot about the self-employment tax part. Definitely do the math carefully!

Doesn't that strategy risk owing penalties if you end up owing too much at tax time? I thought there were rules about having to pay enough throughout the year.

You're right to be concerned about that! You do need to be careful not to underwithhold too much. The general rule is you need to pay at least 90% of your current year tax liability OR 100% of last year's tax liability (110% if your income is over $150,000) through withholding and estimated payments to avoid underpayment penalties. What we did was calculate it pretty closely so we'd either get a very small refund or owe just a little bit. This way we avoided the penalties while also preventing large refunds that would be automatically applied to old debts. It takes a bit more planning, but the IRS has a good withholding calculator on their website that helps make sure you're still meeting the requirements.

Yes, the standard 10-year statute of limitations for IRS collections does apply to shared responsibility payments. The clock starts ticking from the date the tax was assessed, not the tax year itself. So if the assessment happened in 2017 for a 2016 tax issue, the IRS would have until 2027 to collect. Keep in mind that certain actions can extend this timeline, like if the taxpayer requests a payment plan or submits an offer in compromise. But barring any extensions, the IRS generally has 10 years to collect on this type of debt.

Oh no, I had no idea about quarterly payments! How do you even calculate how much to pay each quarter when freelance income is so unpredictable? Do you just guess?

You don't have to guess exactly. The IRS allows you to use the "annualized income installment method" for irregular income. Basically, you calculate your tax based on what you've earned so far in each quarter. Most tax software can help you calculate this, or you can use the IRS Form 1040-ES worksheet. Another approach is to set aside a percentage of each payment you receive (maybe 25-30%) in a separate savings account. Then use that to make your quarterly payments as best you can estimate.

The EITC is great but it's way less helpful for people without kids. I think at $28k for a single person with no dependents the credit is tiny or might not qualify at all. The system is really stacked against childless low-income workers.