Thanks for explaining the hobby loss rule! That's really helpful context. My husband has actually been making small profits consistently (between $1,500-2,000) for the past three years, which I guess would tend to support business classification?

Yes, consistent profits over three years would definitely strengthen the case for business classification. That's one of the key factors the IRS looks at. Since he's showing a consistent pattern of profits, the IRS would be more likely to consider this a business activity rather than a hobby. This actually works in his favor since business expenses are fully deductible against business income, while hobby expenses aren't deductible at all under current tax law. He should definitely consider tracking expenses - he may be paying more tax than necessary by not documenting his costs.

This is great advice. I use a similar system for my side gig. The separate account/card approach makes it super simple to track everything.

I use Direct Pay all the time and its SO much better. You get instant confirmation and can print a receipt. Plus you can schedule payments in advance. No more certified mail costs or wondering if your check is lost! They even send a confirmation email.

I'm definitely going to use Direct Pay next time. This stress isn't worth it. Can you set it up to make quarterly estimated payments automatically, or do you have to manually make each payment?

Oh no, I didn't include a payment voucher! I did write my SSN and "2024 taxes" on the memo line though. Will this cause problems? Is there anything I can do now that it's already mailed?

As long as you wrote your SSN and tax year on the memo line, you should be fine. The payment voucher (Form 1040-V) helps streamline processing, but it's not absolutely required if you've included identifying information on the check itself. If you're concerned, you can always call the IRS after about 21 days to confirm they received and properly applied your payment. Having your SSN on the check is the most important part, which you did right!

What kind of detail do you include in your log? Just dates and who you called, or more specific notes? I'm wondering how detailed I need to be.

I keep it pretty simple. I record the date, contact name, brief purpose (like "client meeting," "vendor call," etc.), and approximate duration. For text messages and emails, I just note weekly totals rather than each individual communication. For social media management, I log the platforms and approximate time spent. The key isn't exhaustive detail - it's consistency. An auditor just wants to see that you maintained records systematically, not that you documented every minute. Also, I take quarterly screenshots of my call logs and text histories as backup. This level of documentation has always been sufficient for me.

I've been using dual-SIM for about 2 years and it works great. You can clearly separate business and personal calls/texts, and most phones let you designate which SIM to use for data. The accounting is a bit trickier though - you'd need to calculate what percentage of the phone use is business-related and only deduct that portion.

18 How do they even manage all those tax filings? Do they just have a team of accountants? And what happens if they make a mistake on one of them? Seems like a nightmare.

2 Most top tennis players have specialized accountants who focus exclusively on international athlete taxation. These firms typically have partners in each major country where tournaments are held, allowing them to file all necessary returns correctly. If they make a mistake, it's typically handled like any other tax error - they may need to file an amended return and potentially pay penalties or interest if it results in underpayment. The bigger challenge is actually keeping track of exactly how many days they spend in each country, as this can affect their tax residency status and reporting obligations.

10 Yes! Athletes can definitely deduct legitimate business expenses against their tournament earnings. Travel, coaching, training, equipment, medical/physiotherapy, agent fees, etc. are all deductible if they're ordinary and necessary for their profession.

Oh wow, I had no idea about the estimated payment requirement. Does that happen automatically, or only if the IRS notices a pattern? And is that $1,000 threshold after applying any withholding I might have, or just based on total tax liability?

The estimated tax requirement is based on your final tax return results - it's not subjective or based on IRS discretion. If you owe more than $1,000 after accounting for any withholding you did have, you're generally required to make estimated payments the following year. The requirement is calculated on your total tax liability minus your withholdings and credits. So if your total tax liability is $10,000 and your withholding was only $8,900, you'd owe $1,100 at filing time - triggering the requirement for quarterly payments the following year. This is a statutory requirement, not a penalty the IRS chooses to impose. It's designed specifically to prevent the kind of strategy you're considering.

I've actually had success with balance transfers combined with a proper withholding adjustment (not going exempt, just adjusting to the correct amount). I got a 15-month 0% offer, transferred my high-interest debt, then adjusted my W-4 to account for legitimate deductions I was eligible for. The extra money in my paychecks went straight to paying down the transferred balance before the 0% period ended.